Tetrahedron letters

Preparation of cyclic disulfides from bisthiocyanates

CJ Burns, LD Field, J Morgan, DD Ridley, V Vignevich

Index: Burns, Christopher J.; Field, Leslie D.; Morgan, Jacqueline; Ridley, Damon D.; Vignevich, Valentina Tetrahedron Letters, 1999 , vol. 40, # 35 p. 6489 - 6492

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Citation Number: 29

Abstract

A mild method for the preparation of disulfides from acyclic bisthiocyanates is presented. The method involves cleavage of thiocyanates with TBAF to form the cyclic disulfides in moderate to good yield. The method can also be applied to the synthesis of acyclic disulfides. Base-sensitive functionalities, such as esters, are unaffected by the reaction conditions.

~35%

~64%

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