title: Novel C-C bond cleavage under mild, neutral conditions: conversion of electron-deficient aryl alkyl ketones to aryl carboxylic esters.
abstract: A novel, unique way to cleave the carbon-carbon bond in aryl alkyl ketones under mild, neutral conditions is described. Treatment of aryl alkyl ketones in a refluxing mixture of N,N-dimethylformamide dimethyl acetal and methanol for 16 h provided aryl carboxylic esters. The scope and limitations of the reaction are discussed. Useful yields of the reaction can be obtained with electron-deficient aryl groups, and the yields are higher when the alkyl group is larger than a methyl group. Studies toward elucidation of the reaction mechanism led to a proposed mechanism that is consistent with all the observations.
authors.affiliation: Chemical Sciences, Wyeth-Ayerst Research, Pearl River, New York 10965 zhangn@war.wyeth.com
authors.forename: Nan
authors.initials: N
authors.lastname: Zhang
authors.forename: Joseph
authors.initials: J
authors.lastname: Vozzolo