Chemical and Pharmaceutical Bulletin

On the synthesis of arylacetones by the Srn 1 arylation of acetone enolate ion.

JF BUNNETT, JE SUNDBERG

Index: Bunnett,J.F.; Sundberg,J.E. Chemical and Pharmaceutical Bulletin, 1975 , vol. 23, p. 2620 - 2628

Full Text: HTML

Citation Number: 45

Abstract

Numerous aryl bromides and iodides react with acetone enolate ion in liquid ammonia under irradiation to form arylacetones in high yield. This synthesis is successful with bromo- or iodobenzene derivatives carrying alkoxy, alkyl, phenyl, halogen, and carboxylate substituents, and with halogen derivatives of polynuclear aromatic hydrocarbons. The method is remarkably insensitive to steric hindrance; for example, 2, 4, 6- ...