Copper(II)-Promoted Aqueous Decomposition of Aldicarb

Article abstract of DOI:10.1021/jo00224a058

The copper(II)-promoted decomposition of aldicarb, 2-methyl-2-(methylthio)propanal O-<(methylamino)carbonyl>oxime, was investigated over the pH region 2.91 to 5.51.The products are 2-methyl-2-(methylthio)propionitrile (82percent) and 2-methyl-2-(methylthio)propanal (18percent).Thus in contrast to many acyl compounds Cu²⁺ promotes the same reaction as that observed in acid rather than the base-catalyzed process.From the effects of Cu²⁺ concentration and temperature upon the rate of reaction a scheme is proposed.Cu²⁺ complexation leads to a β-thioiminium ion whose special stability provides fragmentation as the predominant pathway.