Reaction of derivatives of ?-alkylthio-?-chloroisovaleric acid with ammonia

Abstract

1. The replacement of chlorine by ammonia in anilides of α-alkylthio-β-chloroisovaleric acid in nitromethane, methanol, and water takes place with the formation of an episulfonium ion and results in the formation of anilides of S-alkyl-β,β-dimethylcysteine and isodimethylcysteine. 2. Methyl α-alkylthio-β-chloroisovalerates react with liquid NH3 and its solutions methanol and nitromethane according to a mechanism involving the splitting off of HCl and the addition of NH3. 3. The rate of the splitting off of HCl depends on the nature of the substituent in the alkylthio group, increasing along the series CH3S<C6H5CH2S<C6H5S.