Unprecedented 1,3-acyl shift from alkyl to aryl carbon via a phenyl anion

1 January 1979

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 3,p. 108-110
https://doi.org/10.1039/c39790000108

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 (Bu^tO^––Bu^tOH, 185 °C) in competition with rearrangement through β-enolizable methyl groups and Haller–Bauer type cleavage.

Keywords

ARYL
ALKYL
SHIFT
ACYL
BUTOH
CLEAVAGE
HALLER
ANION
DIPHENYLPENTAN