Reaction of Thiocarboxylic Acids with N-tert-Butyl-2-halo-2-methylpropanimines

Abstract

Reaction of N-tert-butyl-2-chloro-2-methylpropanimine with thiocarboxylic acids has proceeded by two routes, one involving nucleophilic substitution of the chlorine atom in the primary iminium salt by acylthio group, and another via reduction of its cation at the C–Cl bond. Thiocarboxylic acids have reacted with 2-bromoaldimines only via reduction of primary salt cation at the C–Br bond. Acylthio-substituted iminium salts, aldehydes, and their acetals have been prepared.