Thermal 1,3-rearrangement of N-benzoyl-N-methyl-O-thiocarbamoyl-hydroxylamines (thiocarbamoyl N-methylbenzohydroxamates)

Abstract

The preparation and thermal rearrangement of several of the title compounds are described. S-Carbamoyl N-methylbenzothiohydroxamates and the corresponding N-methylbenzamide are the principle products. The rate coefficients for rearrangement change only slightly with variations in the aromatic substituent or solvent polarity, suggesting either a concerted or a free radical pair pathway, rather than mechanisms with a polar or an ionic transition state.