Hard Acid and Soft Nucleophile Systems 10.1) The Mechanistic Study for Debromination of para-Bromoanisole with Aluminum Chloride and Ethanethiol

Halogens of o- or p-halophenols and theirderivatives were reductively removed with the alu-minum chloride and ethanethiol system. Analyses of the dehalogenation products from p-bromoanisole under various conditions uggested that this dehalogenation i volved one-electron oxidation by aluminum chloride at the initial stage. The ESR measurement supported the gener-ation of a radical cation from o- and p-bromoanisoles with aluminum chloride. This radical cation is then stabilized by forming a three-electron bonded species with ethanethiol. Prototropy followed by release of ethanesulfenyl bromide completes the dehalogenation