On the mechanism for loss of CO from aromatic oximes. Evidence for a nucleophilic attack from fluorine labelling

Abstract The mehanisms for loss of CO from benzaldoxime and acetophenone oxime have been investigated with the aid of both fluorine and deuterium labelling as well as field free region metastable peak shapes. Kinetic evergy release data and the metastable ion abundance raion test were used to obtain information about the product ions. It is proposed that loss of CO from both are generated via the nucleophilic attack of the oxygen lone pair eletrons at the ortho position of the phenyl ring as the first step in the reaction sequence.