Facile and efficient stereospecific deamination of aziridines using task-specific silica immobilized organosilane-based nitrite ionic liquid

Facile and efficient stereospecific deamination of aziridines using task-specific silica immobilized organosilane-based nitrite ionic liquid | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Facile and efficient stereospecific deamination of aziridines using task-specific silica immobilized organosilane-based nitrite ionic liquid Hassan Valizadeh, Esmaeil Vesali This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4472508/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 05 Oct, 2024 Read the published version in Monatshefte für Chemie - Chemical Monthly → Version 1 posted 4 You are reading this latest preprint version Abstract Various cis and trans-aziridine derivatives were deaminated via the reaction with task-specific silica immobilized organosilane-based nitrite ionic liquid. Corresponding cis or trans-alkenes were produced as a stereospecific products in good to excellent yields. The advantages of this method include the one-pot procedure, operational simplicity, solvent-free and very short reaction times. Simple handling of this nitrite anione sourse nanoparticles and thus lowering the risks and hazards of a chemical process can offer other important advantages. Aziridine Deamination Nitrite-ionicliquid Solvent-free Introduction Aziridines attracted chemist’s interest not only because of their naturally occurring and strong antibiotic and or antitumor activities, but also because of their structural, thermodynamic, and theoretical aspects. Versatile reactivity of aziridines toward a variety of both electrophilic and nucleophilic reagent have also been attracted the interest of organic chemists [ 1 – 2 ]. Ring opening of ziridines is one of the mostly known reactions and is important in organic synthetic chemistry. This reaction was activated through nucleophilic attack by protonation, quaternization, formation of a Lewis acid adduct, or N–hydrogen replacement with an electron-withdrawing substituent [ 3 – 4 ]. Among the aziridine reactions, deamination of aziridines has been attractive because of their mechanistic, structural, and theoretical aspects. Therefore, numerous methods have been reported for the deamination of aziridine derivatines using various nitrite and nitrosyl derivatives. These reported methods mostly suffer from some disadvantages such as, long reaction times, high costs of preparations, tedious work-up procedures, using of expensive reagents and availability of nitrosation agents [ 5 – 7 ]. Organocatalitic deamination of cis and trans-aziridines in the presence of diethyl thiourea and iodine was reported by Samimi [ 8 ]. Naohiko et al. reported deamination of azafulleroids into C 60 via the oxidation reaction using peracids [ 9 ]. Various aziridine derivatives were reacted with N 2 0 4 in the presence of trimethylamine to give the corresponding olefins under mild reaction conditions [ 10 ]. Toxicity and volatile nature of conventional organic solvents, especially chlorinated hydrocarbons poses a serious threat to the environment [ 11 ]. Nowadays, synthetic organic scientists are strongly taking on the challenge of developing green synthetic methodologies. Therefore, solvent-free synthetic methods have attracted much interest in laboratory and also in the chemical industry [ 12 – 15 ]. Ionic liquids (ILs) are also very good alternative which have been used as a green reaction medium and/or reagent and catalyst in many organic chemistry reactions [ 16 – 18 ]. In connection with our ongoing programs in the use of ILs as a green reaction mediums and reagent and/or catalyst [ 19 – 23 ], we wish to report hear a facile and efficient method for the deamination of aziridines using nitrite ionic liquid immobilized on silica (nirite-IL@silica). This immobilized nitrite ionic liquid can act as a nitrosonium source in this procedure under very mild reaction conditions (Scheme 1 ). Results and Discussion Nitrite-IL@silica nanoparticles was prepared and characterized according the our previously reported method (Scheme 2) [24], and was freshly used in this work. The deamination of E-1-(4-nitrophenyl)-2-benzoylaziridine ( 1a ) was chosen as the typical experiment for the optimization of the reaction. At first the reaction of E-1-(4-nitrophenyl)-2-benzoylaziridine (1 mmol) was studied in the presence of nitrite-IL@silica (1 gr) in tetrahydrofuran at room temperature (Table 1). The progress of the reaction was monitored by TLC. The reaction proceeded smoothly and was completed after 15 min to afford the (E)-1,3-diphenylprop-2-en-1-one ( 2a ) in 29% isolated yield. The typical reaction was also examined at elevated temperature up to refluxing THF and was observed that the yields of the product were decreased. For further investigations, several solvents such as DMF, MeCN, EtOH and CH 2 Cl 2 have been examined in this procedure and no significant change was found in the yield of the products (Table 1, entries 5-8). Then the above described mixture of reactants was moistened with water and the process was tested under solvent-free conditions and found that the reaction was completed in very shorter reaction time (5 min) and significantly in very higher yields (entry 9, Table 1). The typical reaction was examined in ice bath and it was found that the related product was formed in the best yield (94%) in comparison and it was considered as the appropriate conditions. We then investigated the ratio effect of aziridine/nitrite-IL@silica (mmol/gr) and found that the best results were obtained using 1:1.2 ratios. Table 1. Optimization of the reaction. Entry Solvent Temperature (ºC) Time (min) Product 2a Yield a (%) 1 2 3 4 5 6 7 8 9 10 THF THF THF THF DMF EtOH CH 3 CN CH 2 Cl 2 - - rt 45 55 reflux rt rt rt rt rt ice bath 15 8 10 10 35 35 35 35 5 5 29 20 20 15 30 28 32 30 72 94 a Isolated yields. Optimized conditions in hand, we investigated the scope of this reaction, and a range of aziridine derivatives were reacted under these conditions and the results were summarized in Table 2. Using of cis- and trans-2,3-dimethylaziridine, the stereochemical course of deamination process was studied. The results shown in Table 2 (entry 9 and 10), approved that the reaction of all examined trans-aziridines were stereospecific and afforded to trans-alkenes as exclusive products of the deamination reaction. Table 2. Deamination of a variety of aziridines using nitrite-IL@silica. Entry R 1 R 2 R 3 R 4 Reaction Time (min) Product Yield of Product (%) 1 4-NO 2 Ph H H (C=O)Ph 5 2a 94 2 3-OMePh H H (C=O)Ph 5 2b 95 3 3-NO 2 Ph H H (C=O)Ph 6 2c 90 4 p-Cl-Ph H H (C=O)Ph 4 2d 88 5 2-NO 2 Ph H H (C=O)Ph 5 2e 96 6 Ph H H (C=O)Ph 6 2f 98 7 4-OMePh H H (C=O)Ph 5 2g 91 8 Me H Me H 5 2h b 90 9 10 Me Ph H H H Ph Me H 5 6 2i c 2j d 91 94 a Isolated yields, b Cis 2-butene, c Trans 2-butene, d No trans isomer was isolated. For comparison, some of the aziridines shown in Table 2 were deaminated using NaNO 2 instead of the IL@silica, under optimized conditions. The comparable results gathered in Table 3, show the catalytic effect of nitrite-IL@silica and approve that it is a more efficient and viable alternative to the typical nitrite salts which usually are difficult to handle [21]. This nitrite-IL@silica is storable and can be conveniently handled. Table 3. Comparison of the efficiency of sodium nitrite and nitrite-IL@silica. Entry Sodium Nitrite IL@silica Product Yield (%) Product Yield (%) 1 2a 91 2a 94 2 2b 87 2b 92 3 2f 95 2f 98 4 2i 91 2i 96 All of the products were characterised by their spectral data ( 13 C-NMR, 1 H-NMR, IR) and by comparison of the melting points of known products by reported values. Experimental All reagents were purchased from Merck and used without further purification. Perkin Elmer FT-IR spectrometer was used for the determination of infrared spectra. 1 H-NMR spectra were recorded on a Bruker Avance AC- 300 MHz (or 250 MHz) spectrometer and 13 C-NMR spectra at 75.4 MHz (or 62.5 MHz) on the aforementioned instrument. CDCl 3 as the deuterated solvent and TMS as an internal standard were used in NMR analysis. Melting points are uncorrected and measured in open glass-capillaries using Stuart melting point apparatus. General method for deamination reaction Aziridine (1 mmol) and freshly prepared nitrite-IL@silica were mixed thoroughly and was moistened with water at room temperature. The mixture was placed in ice bath and was stired strongly with grining for the time as shown in Table 2. After completion of the reaction, as indicated by TLC (ethyl acetate/ n -hexane, 6/1), deionized water (15 ml) was added and the mixture was extracted with ethyl acetate (25 ml). The extracts were concentrated on a rotary evaporator and the crude mixture was purified by recrystallization from ethanol/ethyl acetate or was purified by silica gel (Merck 230–240 mesh) column chromatography using a ethyl acetate/n-hexane mixture (1:7) as eluent to give pure products 2a – j . (E)-2-(p-nitrophenyl)-3-phenylprop-2-en-1-one (2a): m.p. 165-166 ºC; IR (KBr) (ν max /cm -1 ):: 3062, 3041, 1675, 1589, 1523, 1352, 771. 1 H-NMR (250 MHz, CDCl 3 ): δ 8.31 (m, 2H, ArH), 7.83–7.87 (d, 2H, ArH), 7.82 (m, 2H, ArH), 7.62–7.65 (d, 1H, OlefH), 7.64–7.66 (t, 1H, ArH), 7.56-7.54 (t, 2H, ArH), 7.05 (d, 1H, OlefH), 13 C-NMR (62.5 MHz, CDCl 3 ): δ 189.3, 147.3, 136.3, 134.5, 135.3, 130.5, 128.2, 127.0, 126.8, 126.5, 123.8. (E)-2-(m-methoxyphenyl)-3-phenylprop-2-en-1-one (2b): m.p. 55-57ºC; IR (KBr) (ν max /cm -1 ): 3052, 3039, 1681, 1590, 1520, 1358. 1 H-NMR (250 MHz, CDCl 3 ): δ 8.17 (dd, 1H, ArH), 7.99 (m, 2H), 7.43 (d, 1H, ArH), 7.43 (m, 1H, ArH), 7.83 (m, 1H, ArH), 7.55–7.52 (m, 3H, ArH). 7.42 (d, 1H, OlefH), 7.26 (d, 1H, OlefH), 4.08 (s, 3H, OMe). 13 C-NMR (62.5 MHz, CDCl 3 ): δ 187.3, 148.3, 137.3, 134.4, 135.0, 132.7, 131.2, 129.9, 128.2, 127.0, 126.8, 126.5, 123.8, 56.1. (E)-3-(m-Nitrophenyl)-1-phenylprop-2-en-1-one (2c): Mp 156–160 ºC; IR (KBr): 3051, 1661, 1605, 1580, 1525, 1324, 861, 784, 748, 687. 1 H-NMR (250 MHz, CDCl 3 ): δ 8.53 (s, 1H, ArH), 8.26–8.31 (t, 1H, ArH), 8.0 (m, 2H, ArH), 7.9 (d, 1H, ArH), 7.83 (d, 1H, OlefH), 7.66 (d, 1H, OlefH), 7.62–7.63 (m, 2H, ArH), 7.54 (q, 2H, OlefH). 3 C-NMR (62.5 MHz, CDCl 3 ): δ 190.6, 149.7, 141.3, 136.5, 135.6, 134.1, 132.3, 129.0, 128.6, 128.1, 125.6, 123.5, 121.0. (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (2d): Mp 112–113 ºC; IR (KBr): 3051, 1675, 1612, 1578, 1532, 1318, 876; 1 H-NMR (250 MHz, CDCl 3 ): δ 8.21 (m, 2H, ArH), 7.75(m, 2H, ArH), 7.70(d, 1H, OlefH), 7.55 (m, 2H, ArH), 7.50 (m, 3H, ArH), 7.46 (d, 1H, OlefH): 13 C NMR (62.5 MHz, CDCl3): δ 188.1, 142.2, 138.8, 137.4, 134.4, 132.7, 129.1, 129.5, 127.7, 126.4, 123.1. (E) -3-(2-nitrophenyl)-1-phenylprop-2-en-1-one (2e): m.p. 110-113ºC; IR (KBr) (ν max /cm -1 ): 3042, 3033, 1681, 1598, 891, 783; 1 H-NMR (250 MHz, CDCl 3 ): δ 8.47 (s, 1H, ArH), 8.26-8.28 (m, 1H, ArH), 7.9-8.2 (m, 3H, ArH), 7.79-7.82 (d, 1H, OlefH), 7.62-7.64 (d, 1H, OlefH), 7.62-7.63 (m, 2H, ArH), 7.50-7.53 (m, 2H, ArH). (E)-1,3-Diphenylprop-2-en-1-one (2f): Yellow solid; m.p. 55–57 ºC; IR (KBr) (ν max /cm -1 ): 3052, 3030, 1681(C=O stretching), 1590, 887, 778; 1 H-NMR (250 MHz, CDCl 3 ): δ 7.95-7.92 (m, 2H, ArH), 7.65–7.33 (m, 9H, ArH), 7.23 (d, 1H, J = 10.8 Hz, OlefH); 13 C-NMR (62.5 MHz, CDCl 3 ) (d, ppm): 192.3, 145.1, 136.0, 133.5, 133.4, 129.5, 128.5, 128.4, 127.9, 126.5, 121.2. (E) -3-(3-methoxyphenyl)-1-phenylprop-2-en-1-one (2g): m.p. 52-55ºC; IR (KBr) (ν max /cm -1 ): 3032, 3023, 1687, 1595, 896, 779; 1 H-NMR (250 MHz, CDCl 3 ): δ 8.12-814 (m, 1H, ArH), 7.85-7.89 (m, 2H, ArH), 7.43 (d, 1H, ArH), 7.41-7-43 (m, 1H, ArH), 7.82-7.84 (m, 1H, ArH), 7.53-7.55 (m, 3H, ArH), 7.45 (d, 1H, OlefH), 7.23 (d, 1H, OlefH), 3.88 (s, 3H); 13 C-NMR (62.5 MHz, CDCl 3 ) (d, ppm): 192.0, 164.4, 144.8, 137.3, 136.1, 131.4, 130.9, 121.4, 119.4, 117.6, 111.2, 56.1. (Z) -1,2-Diphenylethene (2j): Oily yellow liquid, IR (KBr) (ν max /cm -1 ): 3018, 3013, 1641, 1590, 812; 1 H-NMR (250 MHz, CDCl 3 ): δ 7.69.7.71 (m, 4H, ArH), 7.41-7.45 (m, 4H, ArH), 7.28-7.31 (2H, ArH), 6.53-6.57 (s, 2H, OlefH); 13 C-NMR (62.5 MHz, CDCl 3 ) (d, ppm): 138.1, 128.9, 127.9, 126.8, 125.7. In conclusion, we have introduced a silica immobilized organosilane-based nitrite ionic liquid as an efficient reagent and catalyst for rapid deamination reaction of aziridines. This reaction can be regarded as a new method for the rapid and stereospecific deamination of aziridines under mild conditions. This approach includes some important aspects such as including a simple handle and storable nitrite source compound and solvent-free conditions which make this method a useful and an attractive procedure for deamination of aziridines. Declarations Acknowledgements The partial financial assistance from the Research Vice Chancellor of AzarbaijanShahidMadani University is gratefully acknowledged. References Schkeryantz JM, Danishefsky SJ, J Am Chem SOC 117:4722. (b), Lim H, Sulikowski GA (eds) (1995) (1996) Tet Lett 37,5243 Padwa A (1996) Comprehensive Heterocyclic Chemistry 11. Vol. lA, Pergamon, Oxford Kump JEG (1991) Comprehensive Organic Synthesis. Fleming Pergamon, Oxford Righi G, Franchini T, Bonini C (1998) Tetrahedron Lett 39:2385 Clark RD, Helmkamp GK (1964) J Org Chem 29:1316 Rundel W, Muller E (1963) Chem Ber 96:2528 Carlson RM, Lee SY (1969) Tetrahedron Lett 10:4001 Samimi HA, Shams Z, Momeni AR (2012) J Iran Chem Soc 9:705 Ikuma N, Fujioka K, Misawa Y, Kokubo K, Oshima T (2015) Org Biomol Chem 13:5038 Lee K, Kim YH (1999) Synth Comm 29:1241 Deka N, Mariotte AM, Boumendjel A (2001) Green Chem 3:263 Choudhary G, Peddinti RK (2011) Green Chem 13:276 Kumar S, Sharma P, Kapoor KK, Hundal MS (2008) Tetrahedron 64:536 Habib PM, Kavala V, Kuo CW, Raihan MJ, Yao CF (2010) Tetrahedron 66:7050 Valizzadeh H, Dinparast L (2012) Monatsh Chem 143:251 Kaur N (2019) Phosphorus Sulfur Silicon Relat Elem 194:165 Valizzadeh H, Gholipour H, Shomali A (2012) Monatsh Chem 143:167 Chen Y, Zhang Q, Zhang F, Li Z, Zhou Y, Qin Y, Xu L, Feng F, Wang Q, Zhang Q, Li X (2024) Appl Catal A: Gen 681:119775 Valizadeh H, Shomali A, Ghorbani J, Nourshargh S (2015) Dyes Pigm 117:117 Valizadeh H, Gholipour H (2011) Compt Rend Chim 14:963 Valizadeh H, Amire M, Gholipour H (2009) J Heterocycl Chem 46:108 Valizadeh H, Fakhari A (2011) Mol Divers 15:1077 Valizadeh H, Amiri M, Khalili E (2012) Mol Div 16:319 Valizadeh H, Amiri M, Hoseinzadeh F (2012) Dyes Pigm 92:1308 Scheme Scheme 1 and 2 are available in the Supplementary Files section. Supplementary Files scheme1.png Scheme 1. Stereospecific deamination of aziridines using nitrite-IL@silica. scheme2.png Scheme 2. Preparation of nitrite-IL@silica. Cite Share Download PDF Status: Published Journal Publication published 05 Oct, 2024 Read the published version in Monatshefte für Chemie - Chemical Monthly → Version 1 posted Reviewers agreed at journal 20 Jun, 2024 Reviewers invited by journal 20 Jun, 2024 Editor assigned by journal 29 May, 2024 First submitted to journal 28 May, 2024 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-4472508","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":316680521,"identity":"edab3186-1baa-4d41-bb78-8051414b640d","order_by":0,"name":"Hassan Valizadeh","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA+klEQVRIiWNgGAWjYBACAxDxAEQe4GF8ABFjbAASzPi1JEC0MBuQoIUBrIVNAkkCtxZzBh7DDwkFdfJ8x3uPVfz4Y5dvcLu5TYKhwjqxAYcWywYeY4kEAzbDmWfOpd3s4Um23HDnIFDLmXScWgzuP0sAauFh3HAjx+wGjwSzgcGNxGYDxrbDuLUcYEv+kWAgYb/h/huzwj8G9VAt//BpYT4GtMUgccMNHjNmnoTDIC2NDxgb8GuxSDBISJ55JsdYWubAcQNJkJaEY+nGuLUwNt/48KfOtu/4GcOPb/5UG/DdSH9w4EONtSwuLThAAmnKR8EoGAWjYBSgAQBZXV2uCVAGlwAAAABJRU5ErkJggg==","orcid":"","institution":"Azarbaijan Shahid Madani University","correspondingAuthor":true,"prefix":"","firstName":"Hassan","middleName":"","lastName":"Valizadeh","suffix":""},{"id":316680522,"identity":"bd92a79c-3120-40f5-89f5-f78ef520139f","order_by":1,"name":"Esmaeil Vesali","email":"","orcid":"","institution":"Payame Noor University","correspondingAuthor":false,"prefix":"","firstName":"Esmaeil","middleName":"","lastName":"Vesali","suffix":""}],"badges":[],"createdAt":"2024-05-24 12:37:12","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-4472508/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-4472508/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s00706-024-03254-9","type":"published","date":"2024-10-05T15:57:08+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":66096744,"identity":"8b0d1649-3f0b-470c-b0c9-47abbae0a82e","added_by":"auto","created_at":"2024-10-07 16:09:01","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":431188,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-4472508/v1/f8304ad8-4382-4431-b5a6-a61b3056a28f.pdf"},{"id":59887813,"identity":"988d9bdf-afad-4db8-848e-7604e0eb20a5","added_by":"auto","created_at":"2024-07-09 01:28:09","extension":"png","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":42163,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 1. \u003c/strong\u003eStereospecific deamination of aziridines using nitrite-IL@silica.\u003c/p\u003e","description":"","filename":"scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-4472508/v1/51e445132f9dd25a2b20c6cc.png"},{"id":59887380,"identity":"a526a4a7-31fb-4be1-bf10-3e05041b3c27","added_by":"auto","created_at":"2024-07-09 01:20:09","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":56160,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 2. \u003c/strong\u003ePreparation of nitrite-IL@silica.\u003c/p\u003e","description":"","filename":"scheme2.png","url":"https://assets-eu.researchsquare.com/files/rs-4472508/v1/fabbac0e94d460fa53214108.png"}],"financialInterests":"","formattedTitle":"Facile and efficient stereospecific deamination of aziridines using task-specific silica immobilized organosilane-based nitrite ionic liquid","fulltext":[{"header":"Introduction","content":"\u003cp\u003eAziridines attracted chemist\u0026rsquo;s interest not only because of their naturally occurring and strong antibiotic and or antitumor activities, but also because of their structural, thermodynamic, and theoretical aspects. Versatile reactivity of aziridines toward a variety of both electrophilic and nucleophilic reagent have also been attracted the interest of organic chemists [\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e]. Ring opening of ziridines is one of the mostly known reactions and is important in organic synthetic chemistry. This reaction was activated through nucleophilic attack by protonation, quaternization, formation of a Lewis acid adduct, or N\u0026ndash;hydrogen replacement with an electron-withdrawing substituent [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. Among the aziridine reactions, deamination of aziridines has been attractive because of their mechanistic, structural, and theoretical aspects. Therefore, numerous methods have been reported for the deamination of aziridine derivatines using various nitrite and nitrosyl derivatives. These reported methods mostly suffer from some disadvantages such as, long reaction times, high costs of preparations, tedious work-up procedures, using of expensive reagents and availability of nitrosation agents [\u003cspan additionalcitationids=\"CR6\" citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e]. Organocatalitic deamination of cis and trans-aziridines in the presence of diethyl thiourea and iodine was reported by Samimi [\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e]. Naohiko et al. reported deamination of azafulleroids into C\u003csub\u003e60\u003c/sub\u003e via the oxidation reaction using peracids [\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e]. Various aziridine derivatives were reacted with N\u003csub\u003e2\u003c/sub\u003e0\u003csub\u003e4\u003c/sub\u003e in the presence of trimethylamine to give the corresponding olefins under mild reaction conditions [\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eToxicity and volatile nature of conventional organic solvents, especially chlorinated hydrocarbons poses a serious threat to the environment [\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e]. Nowadays, synthetic organic scientists are strongly taking on the challenge of developing green synthetic methodologies. Therefore, solvent-free synthetic methods have attracted much interest in laboratory and also in the chemical industry [\u003cspan additionalcitationids=\"CR13 CR14\" citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]. Ionic liquids (ILs) are also very good alternative which have been used as a green reaction medium and/or reagent and catalyst in many organic chemistry reactions [\u003cspan additionalcitationids=\"CR17\" citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e]. In connection with our ongoing programs in the use of ILs as a green reaction mediums and reagent and/or catalyst [\u003cspan additionalcitationids=\"CR20 CR21 CR22\" citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e], we wish to report hear a facile and efficient method for the deamination of aziridines using nitrite ionic liquid immobilized on silica (nirite-IL@silica). This immobilized nitrite ionic liquid can act as a nitrosonium source in this procedure under very mild reaction conditions (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e"},{"header":"Results and Discussion","content":"\u003cp\u003eNitrite-IL@silica nanoparticles was prepared and characterized according the our previously reported method (Scheme 2) [24], \u0026nbsp;and was freshly used in this work.\u003c/p\u003e\n\u003cp\u003eThe deamination of E-1-(4-nitrophenyl)-2-benzoylaziridine (\u003cstrong\u003e1a\u003c/strong\u003e) was chosen as the typical experiment for the optimization of the reaction. At first the reaction of E-1-(4-nitrophenyl)-2-benzoylaziridine (1 mmol) was studied in the presence of nitrite-IL@silica (1 gr) in tetrahydrofuran at room temperature (Table 1). The progress of the reaction was monitored by TLC. The reaction proceeded smoothly and was completed after 15 min to afford the (E)-1,3-diphenylprop-2-en-1-one (\u003cstrong\u003e2a\u003c/strong\u003e) in 29% isolated yield. The typical reaction was also examined at elevated temperature up to refluxing THF and was observed that the yields of the product were decreased. For further investigations, several solvents such as DMF, MeCN, EtOH and CH\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e have been examined in this procedure and no significant change was found in the yield of the products (Table 1, entries 5-8). Then the above described mixture of reactants was moistened with water and the process was tested under solvent-free conditions and found that the reaction was completed in very shorter reaction time (5 min) and significantly in very higher yields (entry 9, Table 1). The typical reaction was examined in ice bath and it was found that the related product was formed in the best yield (94%) in comparison and it was considered as the appropriate conditions. We then investigated the ratio effect of aziridine/nitrite-IL@silica (mmol/gr) and found that the best results were obtained using 1:1.2 ratios.\u003c/p\u003e\n\u003cp\u003eTable\u0026nbsp;1.\u0026nbsp;Optimization of the reaction.\u003c/p\u003e\n\u003cdiv align=\"\"\u003e\n \u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"324\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.814814814814815%\" valign=\"top\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.28395061728395%\" valign=\"top\"\u003e\n \u003cp\u003eSolvent\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"25.925925925925927%\" valign=\"top\"\u003e\n \u003cp\u003eTemperature (\u0026ordm;C)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.74074074074074%\" valign=\"top\"\u003e\n \u003cp\u003eTime (min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"26.234567901234566%\" valign=\"top\"\u003e\n \u003cp\u003eProduct \u003cstrong\u003e2a\u003c/strong\u003e Yield\u003csup\u003ea\u003c/sup\u003e (%)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.814814814814815%\" valign=\"top\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.28395061728395%\" valign=\"top\"\u003e\n \u003cp\u003eTHF\u003c/p\u003e\n \u003cp\u003eTHF\u0026nbsp;\u003c/p\u003e\n \u003cp\u003eTHF\u003c/p\u003e\n \u003cp\u003eTHF\u0026nbsp;\u003c/p\u003e\n \u003cp\u003eDMF\u003c/p\u003e\n \u003cp\u003eEtOH\u003c/p\u003e\n \u003cp\u003eCH\u003csub\u003e3\u003c/sub\u003eCN\u003c/p\u003e\n \u003cp\u003eCH\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"25.925925925925927%\" valign=\"top\"\u003e\n \u003cp\u003ert\u003c/p\u003e\n \u003cp\u003e45\u003c/p\u003e\n \u003cp\u003e55\u003c/p\u003e\n \u003cp\u003ereflux\u0026nbsp;\u003c/p\u003e\n \u003cp\u003ert\u003c/p\u003e\n \u003cp\u003ert\u003c/p\u003e\n \u003cp\u003ert\u003c/p\u003e\n \u003cp\u003ert\u003c/p\u003e\n \u003cp\u003ert\u003c/p\u003e\n \u003cp\u003eice bath\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.74074074074074%\" valign=\"top\"\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003cp\u003e35\u003c/p\u003e\n \u003cp\u003e35\u003c/p\u003e\n \u003cp\u003e35\u003c/p\u003e\n \u003cp\u003e35\u003c/p\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"26.234567901234566%\" valign=\"top\"\u003e\n \u003cp\u003e29\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003cp\u003e28\u003c/p\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003cp\u003e72\u003c/p\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n\u003c/div\u003e\n\u003cp\u003e\u003csup\u003ea\u003c/sup\u003eIsolated yields.\u003c/p\u003e\n\u003cp\u003eOptimized conditions in hand, we investigated the scope of this reaction, and a range of aziridine derivatives were reacted under these conditions and the results were summarized in Table 2. Using of cis- and trans-2,3-dimethylaziridine, the stereochemical course of deamination process was studied. The results shown in Table 2 (entry 9 and 10), approved that the reaction of all examined trans-aziridines were stereospecific and afforded to trans-alkenes as exclusive products of the deamination reaction.\u003c/p\u003e\n\u003cp\u003eTable\u0026nbsp;2. Deamination of a variety of aziridines using nitrite-IL@silica.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003eR\u003csup\u003e1\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eR\u003csup\u003e2\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eR\u003csup\u003e3\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003eR\u003csup\u003e4\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003eReaction Time (min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003eProduct\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003eYield of Product (%)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003e4-NO\u003csub\u003e2\u003c/sub\u003ePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003e3-OMePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2b\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e95\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003e3-NO\u003csub\u003e2\u003c/sub\u003ePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003ep-Cl-Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2d\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003e2-NO\u003csub\u003e2\u003c/sub\u003ePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003ePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2f\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e98\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003e4-OMePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003e(C=O)Ph\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2g\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003eMe\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eMe\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2h\u003csup\u003eb\u003c/sup\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.835341365461847%\" valign=\"top\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.056224899598394%\" valign=\"top\"\u003e\n \u003cp\u003eMe\u003c/p\u003e\n \u003cp\u003ePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.63855421686747%\" valign=\"top\"\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003cp\u003ePh\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.25301204819277%\" valign=\"top\"\u003e\n \u003cp\u003eMe\u003c/p\u003e\n \u003cp\u003eH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.662650602409638%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.048192771084338%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2i\u003csup\u003ec\u003c/sup\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003cp\u003e\u003cstrong\u003e2j\u003csup\u003ed\u003c/sup\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.867469879518072%\" valign=\"top\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003csup\u003ea\u003c/sup\u003eIsolated yields, \u003csup\u003eb\u003c/sup\u003eCis 2-butene, \u003csup\u003ec\u003c/sup\u003eTrans 2-butene, \u003csup\u003ed\u003c/sup\u003eNo trans isomer was isolated.\u003c/p\u003e\n\u003cp\u003eFor comparison, some of the aziridines shown in Table 2 were deaminated using NaNO\u003csub\u003e2\u003c/sub\u003e instead of the IL@silica, under optimized conditions. The comparable results gathered in Table 3, show the catalytic effect of nitrite-IL@silica and approve that it is a more efficient and viable alternative to the typical nitrite salts which usually are difficult to handle [21]. This nitrite-IL@silica is storable and can be conveniently handled.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eTable\u0026nbsp;3. Comparison of the efficiency of sodium nitrite and nitrite-IL@silica.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.925373134328359%\" rowspan=\"2\" valign=\"top\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"4.477611940298507%\" valign=\"top\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"42.039800995024876%\" colspan=\"2\" valign=\"top\"\u003e\n \u003cp\u003eSodium Nitrite\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"38.55721393034826%\" colspan=\"2\" valign=\"top\"\u003e\n \u003cp\u003eIL@silica\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"5.2631578947368425%\" valign=\"top\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"25.43859649122807%\" valign=\"top\"\u003e\n \u003cp\u003eProduct\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.976608187134502%\" valign=\"top\"\u003e\n \u003cp\u003eYield (%)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"25.43859649122807%\" valign=\"top\"\u003e\n \u003cp\u003eProduct\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.883040935672515%\" valign=\"top\"\u003e\n \u003cp\u003eYield (%)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.925373134328359%\" valign=\"top\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"4.477611940298507%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.398009950248756%\" valign=\"top\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.915422885572138%\" valign=\"top\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.925373134328359%\" valign=\"top\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"4.477611940298507%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2b\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.398009950248756%\" valign=\"top\"\u003e\n \u003cp\u003e87\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2b\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.915422885572138%\" valign=\"top\"\u003e\n \u003cp\u003e92\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.925373134328359%\" valign=\"top\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"4.477611940298507%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2f\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.398009950248756%\" valign=\"top\"\u003e\n \u003cp\u003e95\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2f\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.915422885572138%\" valign=\"top\"\u003e\n \u003cp\u003e98\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"14.925373134328359%\" valign=\"top\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"4.477611940298507%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2i\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.398009950248756%\" valign=\"top\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"21.64179104477612%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cstrong\u003e2i\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.915422885572138%\" valign=\"top\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eAll of the products were characterised by their spectral data (\u003csup\u003e13\u003c/sup\u003eC-NMR, \u003csup\u003e1\u003c/sup\u003eH-NMR, IR) and by comparison of the melting points of known products by reported values.\u003c/p\u003e"},{"header":"Experimental","content":"\u003cp\u003eAll reagents were purchased from Merck and used without further purification. \u0026nbsp; Perkin Elmer FT-IR spectrometer was used for the determination of infrared spectra. \u003csup\u003e1\u003c/sup\u003eH-NMR spectra were recorded on a Bruker Avance AC- 300 MHz (or 250 MHz) spectrometer and \u003csup\u003e13\u003c/sup\u003eC-NMR spectra at 75.4 MHz (or 62.5 MHz) on the aforementioned instrument. CDCl\u003csub\u003e3\u003c/sub\u003e as the deuterated solvent and TMS as an internal standard were used in NMR analysis. Melting points are uncorrected and measured in open glass-capillaries using Stuart melting point apparatus.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003eGeneral method for deamination reaction\u003c/em\u003e\u003c/p\u003e\n\u003cp\u003eAziridine (1 mmol) and freshly prepared nitrite-IL@silica were mixed thoroughly and was moistened with water at room temperature. The mixture was placed in ice bath and\u0026nbsp;was stired strongly with grining for the time as shown in Table 2. After completion of the reaction, as indicated by TLC (ethyl acetate/\u003cem\u003en\u003c/em\u003e-hexane, 6/1), deionized water (15 ml) was added and the mixture was extracted with ethyl acetate (25 ml). The extracts were concentrated on a rotary evaporator and the crude mixture was purified by recrystallization from ethanol/ethyl acetate or\u0026nbsp;was purified by silica gel (Merck 230\u0026ndash;240 mesh) column chromatography using a ethyl acetate/n-hexane mixture (1:7) as eluent to give pure products \u003cstrong\u003e2a\u003c/strong\u003e\u0026ndash;\u003cstrong\u003ej\u003c/strong\u003e.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cem\u003e(E)-2-(p-nitrophenyl)-3-phenylprop-2-en-1-one\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;(2a):\u003c/strong\u003e m.p. 165-166 \u0026ordm;C; IR (KBr)\u0026nbsp;(\u0026nu;\u003csub\u003emax\u003c/sub\u003e/cm\u003csup\u003e-1\u003c/sup\u003e):: 3062, 3041, 1675,\u0026nbsp;1589, 1523, 1352, 771. \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;8.31 (m, 2H, ArH), 7.83\u0026ndash;7.87 (d, 2H, ArH), 7.82 (m, 2H, ArH), 7.62\u0026ndash;7.65 (d, 1H, OlefH), 7.64\u0026ndash;7.66 (t, 1H, ArH), 7.56-7.54 (t, 2H, ArH), 7.05 (d, 1H, OlefH), \u003csup\u003e13\u003c/sup\u003eC-NMR (62.5 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;189.3, 147.3, 136.3, 134.5, 135.3, 130.5, 128.2, 127.0, 126.8, 126.5, 123.8.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cem\u003e(E)-2-(m-methoxyphenyl)-3-phenylprop-2-en-1-one\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;(2b):\u003c/strong\u003e m.p. 55-57\u0026ordm;C; IR (KBr)\u0026nbsp;(\u0026nu;\u003csub\u003emax\u003c/sub\u003e/cm\u003csup\u003e-1\u003c/sup\u003e):\u0026nbsp;3052, 3039, 1681,\u0026nbsp;1590, 1520, 1358. \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;8.17 (dd, 1H, ArH), 7.99 (m, 2H), 7.43 (d, 1H, ArH), 7.43 (m, 1H, ArH), 7.83 (m, 1H, ArH), 7.55\u0026ndash;7.52 (m, 3H, ArH). 7.42 (d, 1H, OlefH), 7.26 (d, 1H, OlefH), 4.08 (s, 3H, OMe). \u003csup\u003e13\u003c/sup\u003eC-NMR (62.5 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;187.3, 148.3, 137.3, 134.4, 135.0, 132.7, 131.2, 129.9, 128.2, 127.0, 126.8, 126.5, 123.8, 56.1.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cem\u003e(E)-3-(m-Nitrophenyl)-1-phenylprop-2-en-1-one\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;(2c):\u003c/strong\u003e Mp 156\u0026ndash;160 \u0026ordm;C; IR (KBr): 3051, 1661, 1605, 1580, 1525, 1324, 861, 784, 748, 687. \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;8.53 (s, 1H, ArH), 8.26\u0026ndash;8.31 (t, 1H, ArH), 8.0 (m, 2H, ArH), 7.9 (d, 1H, ArH), 7.83 (d, 1H, OlefH), 7.66 (d, 1H, OlefH), 7.62\u0026ndash;7.63 (m, 2H, ArH), 7.54 (q, 2H, OlefH). \u003csup\u003e3\u003c/sup\u003eC-NMR (62.5 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;190.6, 149.7, 141.3, 136.5, 135.6, 134.1, 132.3, 129.0, 128.6, 128.1, 125.6, 123.5, 121.0.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cem\u003e(E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one\u0026nbsp;\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e(2d):\u003c/strong\u003e Mp 112\u0026ndash;113 \u0026ordm;C; IR (KBr): 3051, 1675, 1612, 1578, 1532, 1318, 876; \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;8.21 (m, 2H, ArH), 7.75(m, 2H, ArH), 7.70(d, 1H, OlefH), 7.55 (m, 2H, ArH), 7.50 (m, 3H, ArH), 7.46 (d, 1H, OlefH): \u003csup\u003e13\u003c/sup\u003eC NMR (62.5 MHz, CDCl3):\u0026nbsp;\u0026delta;\u0026nbsp;188.1, 142.2, 138.8, 137.4, 134.4, 132.7, 129.1, 129.5, 127.7, 126.4, 123.1.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e(E)\u003cem\u003e-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u003cem\u003e\u0026nbsp;\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e(2e):\u0026nbsp;\u003c/strong\u003em.p. 110-113\u0026ordm;C; IR (KBr)\u0026nbsp;(\u0026nu;\u003csub\u003emax\u003c/sub\u003e/cm\u003csup\u003e-1\u003c/sup\u003e):\u0026nbsp;3042, 3033, 1681, 1598, 891, 783; \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;8.47 (s, 1H, ArH), 8.26-8.28 (m, 1H, ArH), 7.9-8.2 (m, 3H, ArH), 7.79-7.82 (d, 1H, OlefH), 7.62-7.64 (d, 1H, OlefH), 7.62-7.63 (m, 2H, ArH), 7.50-7.53 (m, 2H, ArH).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cem\u003e(E)-1,3-Diphenylprop-2-en-1-one\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;(2f):\u0026nbsp;\u003c/strong\u003eYellow solid; m.p. 55\u0026ndash;57 \u0026ordm;C; IR (KBr)\u0026nbsp;(\u0026nu;\u003csub\u003emax\u003c/sub\u003e/cm\u003csup\u003e-1\u003c/sup\u003e):\u0026nbsp;3052, 3030, 1681(C=O stretching),\u0026nbsp;1590, 887, 778; \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;7.95-7.92 (m, 2H, ArH), 7.65\u0026ndash;7.33 (m, 9H,\u0026nbsp;ArH), 7.23 (d, 1H, J = 10.8 Hz, OlefH); \u003csup\u003e13\u003c/sup\u003eC-NMR (62.5 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) (d, ppm): 192.3, 145.1, 136.0, 133.5, 133.4, 129.5, 128.5, 128.4, 127.9, 126.5, 121.2.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e(E)\u003cem\u003e-3-(3-methoxyphenyl)-1-phenylprop-2-en-1-one\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u003cem\u003e\u0026nbsp;\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e(2g):\u0026nbsp;\u003c/strong\u003em.p. 52-55\u0026ordm;C; IR (KBr)\u0026nbsp;(\u0026nu;\u003csub\u003emax\u003c/sub\u003e/cm\u003csup\u003e-1\u003c/sup\u003e):\u0026nbsp;3032, 3023, 1687, 1595, 896, 779; \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;8.12-814 (m, 1H, ArH), 7.85-7.89 (m, 2H, ArH), 7.43 (d, 1H, ArH), 7.41-7-43 (m, 1H, ArH), 7.82-7.84 (m, 1H, ArH), 7.53-7.55 (m, 3H, ArH), 7.45 (d, 1H, OlefH), 7.23 (d, 1H, OlefH), 3.88 (s, 3H);\u0026nbsp;\u003csup\u003e13\u003c/sup\u003eC-NMR (62.5 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) (d, ppm): 192.0, 164.4, 144.8, 137.3, 136.1, 131.4, 130.9, 121.4, 119.4, 117.6, 111.2, 56.1.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e(Z)\u003cem\u003e-1,2-Diphenylethene\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u003cem\u003e\u0026nbsp;\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e(2j):\u003c/strong\u003e Oily yellow liquid,\u0026nbsp;IR (KBr)\u0026nbsp;(\u0026nu;\u003csub\u003emax\u003c/sub\u003e/cm\u003csup\u003e-1\u003c/sup\u003e):\u0026nbsp;3018, 3013, 1641, 1590, 812; \u003csup\u003e1\u003c/sup\u003eH-NMR (250 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e):\u0026nbsp;\u0026delta;\u0026nbsp;7.69.7.71 (m, 4H, ArH), 7.41-7.45 (m, 4H, ArH), 7.28-7.31 (2H, ArH), 6.53-6.57 (s, 2H, OlefH); \u003csup\u003e13\u003c/sup\u003eC-NMR (62.5 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) (d, ppm): 138.1, 128.9, 127.9, 126.8, 125.7.\u003c/p\u003e\n\u003cp\u003eIn conclusion, we have introduced a silica immobilized organosilane-based nitrite ionic liquid as an efficient reagent and catalyst for rapid deamination reaction of aziridines. This reaction can be regarded as a new method for the rapid and stereospecific deamination of aziridines under mild conditions. This approach includes some important aspects such as including a simple handle and storable nitrite source compound and solvent-free conditions which make this method a useful and an attractive procedure for deamination of aziridines.\u003c/p\u003e"},{"header":"Declarations","content":"\u003ch2\u003eAcknowledgements\u003c/h2\u003e \u003cp\u003eThe partial financial assistance from the Research Vice Chancellor of AzarbaijanShahidMadani University is gratefully acknowledged.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eSchkeryantz JM, Danishefsky SJ, J Am Chem SOC 117:4722. (b), Lim H, Sulikowski GA (eds) (1995) (1996) Tet Lett 37,5243\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003ePadwa A (1996) Comprehensive Heterocyclic Chemistry 11. Vol. lA, Pergamon, Oxford\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eKump JEG (1991) Comprehensive Organic Synthesis. Fleming Pergamon, Oxford\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eRighi G, Franchini T, Bonini C (1998) Tetrahedron Lett 39:2385\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eClark RD, Helmkamp GK (1964) J Org Chem 29:1316\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eRundel W, Muller E (1963) Chem Ber 96:2528\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eCarlson RM, Lee SY (1969) Tetrahedron Lett 10:4001\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eSamimi HA, Shams Z, Momeni AR (2012) J Iran Chem Soc 9:705\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eIkuma N, Fujioka K, Misawa Y, Kokubo K, Oshima T (2015) Org Biomol Chem 13:5038\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eLee K, Kim YH (1999) Synth Comm 29:1241\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eDeka N, Mariotte AM, Boumendjel A (2001) Green Chem 3:263\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eChoudhary G, Peddinti RK (2011) Green Chem 13:276\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eKumar S, Sharma P, Kapoor KK, Hundal MS (2008) Tetrahedron 64:536\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eHabib PM, Kavala V, Kuo CW, Raihan MJ, Yao CF (2010) Tetrahedron 66:7050\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizzadeh H, Dinparast L (2012) Monatsh Chem 143:251\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eKaur N (2019) Phosphorus Sulfur Silicon Relat Elem 194:165\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizzadeh H, Gholipour H, Shomali A (2012) Monatsh Chem 143:167\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eChen Y, Zhang Q, Zhang F, Li Z, Zhou Y, Qin Y, Xu L, Feng F, Wang Q, Zhang Q, Li X (2024) Appl Catal A: Gen 681:119775\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizadeh H, Shomali A, Ghorbani J, Nourshargh S (2015) Dyes Pigm 117:117\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizadeh H, Gholipour H (2011) Compt Rend Chim 14:963\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizadeh H, Amire M, Gholipour H (2009) J Heterocycl Chem 46:108\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizadeh H, Fakhari A (2011) Mol Divers 15:1077\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizadeh H, Amiri M, Khalili E (2012) Mol Div 16:319\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eValizadeh H, Amiri M, Hoseinzadeh F (2012) Dyes Pigm 92:1308\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"},{"header":"Scheme ","content":"\u003cp\u003eScheme 1 and 2 are available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"monatshefte-fur-chemie-chemical-monthly","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"mccm","sideBox":"Learn more about [Monatshefte für Chemie - Chemical Monthly](https://www.springer.com/journal/706)","snPcode":"706","submissionUrl":"https://www.editorialmanager.com/mccm/","title":"Monatshefte für Chemie - Chemical Monthly","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Aziridine , Deamination , Nitrite-ionicliquid , Solvent-free","lastPublishedDoi":"10.21203/rs.3.rs-4472508/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4472508/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eVarious cis and trans-aziridine derivatives were deaminated via the reaction with task-specific silica immobilized organosilane-based nitrite ionic liquid. Corresponding cis or trans-alkenes were produced as a stereospecific products in good to excellent yields. The advantages of this method include the one-pot procedure, operational simplicity, solvent-free and very short reaction times. Simple handling of this nitrite anione sourse nanoparticles and thus lowering the risks and hazards of a chemical process can offer other important advantages.\u003c/p\u003e","manuscriptTitle":"Facile and efficient stereospecific deamination of aziridines using task-specific silica immobilized organosilane-based nitrite ionic liquid","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-07-09 01:20:04","doi":"10.21203/rs.3.rs-4472508/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"reviewerAgreed","content":"","date":"2024-06-20T05:51:34+00:00","index":0,"fulltext":""},{"type":"reviewersInvited","content":"","date":"2024-06-20T05:35:40+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2024-05-29T14:51:27+00:00","index":"","fulltext":""},{"type":"submitted","content":"Monatshefte für Chemie - Chemical Monthly","date":"2024-05-28T10:51:40+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"monatshefte-fur-chemie-chemical-monthly","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"mccm","sideBox":"Learn more about [Monatshefte für Chemie - Chemical Monthly](https://www.springer.com/journal/706)","snPcode":"706","submissionUrl":"https://www.editorialmanager.com/mccm/","title":"Monatshefte für Chemie - Chemical Monthly","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"61cee4a8-c0e9-48a2-85ed-d6df27fadd4c","owner":[],"postedDate":"July 9th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2024-10-07T15:59:47+00:00","versionOfRecord":{"articleIdentity":"rs-4472508","link":"https://doi.org/10.1007/s00706-024-03254-9","journal":{"identity":"monatshefte-fur-chemie-chemical-monthly","isVorOnly":false,"title":"Monatshefte für Chemie - Chemical Monthly"},"publishedOn":"2024-10-05 15:57:08","publishedOnDateReadable":"October 5th, 2024"},"versionCreatedAt":"2024-07-09 01:20:04","video":"","vorDoi":"10.1007/s00706-024-03254-9","vorDoiUrl":"https://doi.org/10.1007/s00706-024-03254-9","workflowStages":[]},"version":"v1","identity":"rs-4472508","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-4472508","identity":"rs-4472508","version":["v1"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}