Relative migratory aptitudes in the Schmidt reaction of arylpropanones and 2-arylcyclohexanones

Abstract

The relative migratory aptitude of benzyl and alkyl groups in the reaction of arylpropanones and 2-arylcyclohexanones with hydrazoic acid depends on the solvent, temperature and nature of the substituents in the aryl ring. It is suggested that at low temperatures electron- donating groups in the aromatic ring favour a charge-transfer interaction which affects the relative migratory aptitudes.