The anomalous Schmidt reactions of acrylic acid and its esters and acrylonitrile

Abstract

Interaction of acrylic acid and hydrazoic acid in the presence of hydrochloric acid or sulphuric acid gives considerable quantities of pyruvic acid and ammonia; the mechanism of the reaction, which is believed to proceed through the intermediate formation of 3-azidopropionic acid, is discussed. Reactions between hydrazoic acid and methyl acrylate, ethyl acrylate, and acrylonitrile in the presence of hydrochloric or sulphuric acid are described and discussed. The preparation and acid-catalysed decomposition of 3-azidopropionic acid, methyl and ethyl 3-azidopropionates, and 3-azidopropionitrile are reported.