A Green and Facile Method for the Synthesis of Substituted 1,2-Epoxy Ethylgembisphosphonates and their Symmetrical Dibutylammmonium Salts

2020 · doi:10.3762/bxiv.2020.3.v1
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Abstract

In this paper we report a convenient and environmentally friendly method for the synthesis of substituted 1,2-epoxy ethyl gem bisphosphonates using hydrogen peroxide in methanol-water solvent system. This reaction allows easy access to the desired epoxy bisphosphonates in good to excellent yields. It can also be scaled up easily since it requires small amounts of solvents and there are no by-products. The epoxy bisphosphonates were dealkylated with dibutylamine under solvent-free conditions to give novel symmetrical dibutylammonium diethyl (oxirane-2,2-diyl)bisphosphonate salts.
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Materials

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry In this paper we report a convenient and environmentally friendly method for the synthesis of substituted 1,2-epoxy ethylgembisphosphonates using hydrogen peroxide in methanol-water solvent system. This reaction allows easy access to the desired epoxy bisphosphonates in good to excellent yields. It can also be scaled up easily since it requires small amounts of solvents and there are no by-products. The epoxy bisphosphonates were dealkylated with dibutylamine under solvent-free conditions to give novel symmetrical dibutylammonium diethyl (oxirane-2,2-diyl)bisphosphonate salts.

Keywords

Epoxy bisphosphonates; Green epoxidation; Electron-deficient alkenes; Dealkylation; Ammmonium bisphosphonate salts. | Format: DOCX | Size: 2.1 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Simelane, S. B.; Ndinteh, D. T.; Mbianda, X. Y. Beilstein Arch. 2020, 20203. doi:10.3762/bxiv.2020.3.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2020 Simelane et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

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