Head-to-Tail Packing to Facilitate [2+2] Cycloaddition for Green Synthesis of Cyclobutane Derivatives in Specific Configuration

Head-to-Tail Packing to Facilitate [2+2] Cycloaddition for Green Synthesis of Cyclobutane Derivatives in Specific Configuration | Authorea try { document.documentElement.classList.add('js'); } catch (e) { } var _gaq = _gaq || []; _gaq.push(['_setAccount', 'G-8VDV14Y67G']); _gaq.push(['_trackPageview']); (function() { var ga = document.createElement('script'); ga.type = 'text/javascript'; ga.async = true; ga.src = ('https:' == document.location.protocol ? 'https://ssl' : 'http://www') + '.google-analytics.com/ga.js'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(ga, s); })(); Skip to main content Preprints Collections Wiley Open Research IET Open Research Ecological Society of Japan All Collections About About Authorea FAQs Contact Us Quick Search anywhere Search for preprint articles, keywords, etc. Search Search ADVANCED SEARCH SCROLL This is a preprint and has not been peer reviewed. Data may be preliminary. 24 January 2025 V1 Latest version Share on Head-to-Tail Packing to Facilitate [2+2] Cycloaddition for Green Synthesis of Cyclobutane Derivatives in Specific Configuration Authors : Xiqiao Yang , Liuyang Jin , Jingbo Sun , Yuan Yue , Kaiqi Ye , Cheng Liu , Chao Chen , Liang Li , Panče Naumov , and Ran Lu 0000-0003-0486-532X [email protected] Authors Info & Affiliations https://doi.org/10.22541/au.173770396.67178180/v1 Published Chemistry – A European Journal Version of record Peer review timeline 383 views 229 downloads Contents Abstract Supplementary Material Information & Authors Metrics & Citations View Options References Figures Tables Media Share Abstract Topological [2+2] cycloaddition is known to provide a convenient synthetic route for cyclobutane derivatives from favourably dispositioned dienes. In this study, new diphenylpenta-2,4-dienenitrile derivatives (abbreviated as HDE , MeDE , ClDE , BrDE , MeODE and MeNDE ) were synthesized, and their reactivity and selectivity were investigated in relation to their molecular packing in the respective crystals. HDE and MeDE , with head-to-tail (HT) arrangement, yielded only one type of photodimer with high activities. On the contrary, ClDE and BrDE , with head-to-head (HH) packing, reacted to a mixture of photoproducts with low activities. This observation may be due to the strong non-covalent interactions between the potentially reactive olefin pairs as suggested by energy decomposition analysis. Furthermore, the reaction activation energies for photodimerization of the HT-packed olefin pairs are indeed lower than those of the HH-arranged ones. The HT packing of the diphenyldienes not only enhances the reactivity in the topological [2+2] cycloaddition but also contributes chemospecificity, regiospecifity and stereospecificity, all of which are essential for preparation of specific cyclobutanes derivatives based on photodimerization. Supplementary Material File (manuscript.pdf) Download 709.16 KB Information & Authors Information Version history V1 Version 1 24 January 2025 Peer review timeline Published Chemistry – A European Journal Version of Record 27 Mar 2025 Published Copyright This work is licensed under a Non Exclusive No Reuse License. Keywords chemoselectivity conjugated dienes photoactuation stereospecificity topological [2+2] cycloaddition Authors Affiliations Xiqiao Yang Jilin University College of Chemistry View all articles by this author Liuyang Jin Jilin University College of Chemistry View all articles by this author Jingbo Sun Jilin University College of Chemistry View all articles by this author Yuan Yue Jilin University College of Chemistry View all articles by this author Kaiqi Ye Jilin University College of Chemistry View all articles by this author Cheng Liu Jilin University College of Chemistry View all articles by this author Chao Chen Jilin University College of Chemistry View all articles by this author Liang Li New York University Abu Dhabi View all articles by this author Panče Naumov New York University Abu Dhabi View all articles by this author Ran Lu 0000-0003-0486-532X [email protected] Jilin University College of Chemistry View all articles by this author Metrics & Citations Metrics Article Usage 383 views 229 downloads .FvxKWukQNSOunydq8rnd { width: 100px; } Citations Download citation Xiqiao Yang, Liuyang Jin, Jingbo Sun, et al. Head-to-Tail Packing to Facilitate [2+2] Cycloaddition for Green Synthesis of Cyclobutane Derivatives in Specific Configuration. Authorea . 24 January 2025. DOI: https://doi.org/10.22541/au.173770396.67178180/v1 If you have the appropriate software installed, you can download article citation data to the citation manager of your choice. Simply select your manager software from the list below and click Download. For more information or tips please see 'Downloading to a citation manager' in the Help menu . Format Please select one from the list RIS (ProCite, Reference Manager) EndNote BibTex Medlars RefWorks Direct import Tips for downloading citations document.getElementById('citMgrHelpLink').addEventListener('click', function() { popupHelp(this.href); return false; }); $(".js__slcInclude").on("change", function(e){ if ($(this).val() == 'refworks') $('#direct').prop("checked", false); $('#direct').prop("disabled", ($(this).val() == 'refworks')); }); Cited by Vishnukumar Thanasekar, Aritra Bhowmik, Manish Kumar Mishra, Soumyajit Ghosh, Mechanically Flexible Pentadienenitrile Derivative-Based Molecular Crystals Exhibiting Distinct Photoresponsive Behavior, Crystal Growth & Design, (2026). https://doi.org/10.1021/acs.cgd.6c00326 Crossref Loading... View Options View options PDF View PDF Figures Tables Media Share Share Share article link Copy Link Copied! Copying failed. 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