The Synthesis of Thiocarboxylic Acids by the Reaction of Acid Halide-N, N-Dimethylthioformamide Adducts with Hydrogen Sulfide

Abstract

The thiolysis of acid halide-N, N-dimethylthioformamide (DMTF) adducts has been investigated. In this reaction, aliphatic, alicyclic, aromatic, substituted aromatic acid halides and these dibasic acid halides gave the corresponding thiocarboxylic acids in quantitative yield.
Thiocarboxylic acid, in the presence of hydrogen sulfide, was preferentially generated from the reaction of the adduct with acid halide via acid thioanhydride rather than the direct cleavage of C-S bond of the adduct.