2-Trimethylsilylethyl sulfides in the von Braun cyanogen bromide reaction: selective preparation of thiocyanates and application to nucleoside chemistry

S Chambert, F Thomasson…

文献索引：Chambert, Stephane; Thomasson, Francois; Decout, Jean-Luc Journal of Organic Chemistry, 2002 , vol. 67, # 6 p. 1898 - 1904

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被引用次数: 23

摘要

Mixed 2-(trimethylsilyl) ethyl sulfides were synthesized and used in the von Braun cyanogen bromide reaction for preparing selectively thiocyanates in high yield. We show here that this cleavage reaction is highly selective in methanol in comparison with the reaction of the corresponding non-silyl sulfide analogues. This reaction was applied to the synthesis of nucleosidic thiocyanates such as the new nucleosides 14 and 18 in the search for ...