Utilisation of sulphur-containing leaving groups. Part 2. Monitored reduction of carboxylic acids into alcohols or aldehydes via 3-acylthiazolidine-2-thiones by sodium rorohydride or di-isobutylaluminium hydride

Abstract

3-Acylthiazolidine-2-thiones (2) have been prepared by three methods, and treated with di-isobutylaluminium hydride or sodium borohydride to give aldehyde or alcohol in high yield, respectively. The original yellow colour disappears when reduction is finished, enabling the reaction to be monitored. The high reactivity of the carbonyl group in amide (2) was briefly discussed.