An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates |
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Authors: | Slawomir Lach Sebastian DemkowiczDariusz Witt |
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Affiliation: | Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, Gdansk 80-233, Poland |
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Abstract: | We have developed convenient methods for the synthesis of functionalized unsymmetrical dialkyl disulfides under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives 1 with functionalized alkyl thiolate anions, generated in situ from thioacetates 2 and sodium methoxide or butylamine. The developed method allows the preparation of unsymmetrical disulfides bearing additional hydroxy, carboxy, amino, azido, biotin, or maleimide functionalities. |
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Keywords: | Unsymmetrical disulfides Thiolate Phosphorodithioic acid Thioacetates Biotin |
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