Reaction of N-tert-butyl-2-haloaldimines with thiolcarboxylic acids

Abstract

The reactions of N-tert-butyl-2-chloroaldimine with thiolcarboxylic acids occurs along two pathways: nucleophilic substitution of chlorine in the primary iminium salt by acylmercapto group and reduction of the C–Cl bond in the iminium cation. The reactions of thiolcarboxylic acids reaction with 2-bromoaldimine take exclusively the second pathway, specifically reduction of the C–Br bond in the cation of the primary iminium salt. Acylmercapro-substituted iminium salts and aldehydes and their acetals are synthesized.