The Journal of Organic Chemistry

Multiple Reaction Channels of (N-Acyl-N-alkylcarbamoyl) oxyl Radicals from N-Acyl PTOC Carbamates

JL Esker, M Newcomb

Index: Esker, John L.; Newcomb, Martin Journal of Organic Chemistry, 1994 , vol. 59, # 10 p. 2779 - 2786

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Citation Number: 37

Abstract

N-Acyl-N-alkyl-N'-hydroxypyridine-2-thione carbamates (N-acyl PTOC carbamates) 1 are prepared in good to excellent yield by reactions of N-acylcarbamoyl chlorides with N- hydroxypyridine-2-thione sodium salt. Methods for production of the requisite carbamoyl chlorides by reaction of a secondary amide with trimethylsilyl triflate followed by treatment with phosgene were optimized. Precursors 1 react in radical chain reactions to give the ...