Synthesis and reactions of some pyrrolethiols

Abstract

A number of pyrrolethiols have been prepared by the alkaline hydrolysis of the corresponding S-pyrrolylisothiouronium salts. Although generally too reactive to be isolated unless stabilized by electron-withdrawing substituents in the pyrrole ring, these compounds have proved reliable intermediates and undergo the usual reactions of thiols, e.g. acylation, alkylation, oxidation, and addition to acetylenes, isocyanates, and isothiocyanates. Two relatively stable pyrrolethiols have been fully characterized and spectral evidence indicates that they exist in the thiol form.