Journal
TETRAHEDRON LETTERS
Volume 54, Issue 51, Pages 7021-7023Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.10.056
Keywords
Unsymmetrical disulfides; Thiolate; Phosphorodithioic acid; Thioacetates; Biotin
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Funding
- Polish Ministry of Science and Higher Education [N N204 208440]
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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. (C) 2013 Elsevier Ltd. All rights reserved.
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