A new procedure for the conversion of thiols into reactive sulfenylating agents

DHR Barton, RH Hesse, AC O'Sullivan…

Index: Barton, D. H. R.; Hesse, R. H.; O'Sullivan, A. C.; Pechet, M. M. Journal of Organic Chemistry, 1991 , vol. 56, # 23 p. 6697 - 6702

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Citation Number: 23

Abstract

Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agenta (eg, alkyl fluorosulfonates or oxonium salta) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme 11) and react smoothly with a variety of sulfur nucleophiles (eg, thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides ...