Unprecedented 1,3-acyl shift from alkyl to aryl carbon via a phenyl anion
Abstract
A 1,3-shift of an acyl group from sp3 to sp2 carbon is exhibited by 2-methyl- and 2,4-dimethyl-2,4-diphenylpentan-3-one under strongly basic conditions (ButO––ButOH, 185 °C) in competition with rearrangement through β-enolizable methyl groups and Haller–Bauer type cleavage.