Tetrahedron

O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide.

DHR Barton, JC Jaszberenyi, EA Theodorakis

Index: Barton, Derek H. R.; Jaszberenyi, Joseph Cs.; Theodorakis, Emmanouil A. Tetrahedron, 1991 , vol. 47, # 44 p. 9167 - 9178

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Citation Number: 10

Abstract

Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1, 8-diazabicyclo [5.4. 0] under-7-ene (DBU) or 1, 4-diazabicyclo [2.2. 2] octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.