Document Detail


Novel C-C bond cleavage under mild, neutral conditions: conversion of electron-deficient aryl alkyl ketones to aryl carboxylic esters.
MedLine Citation:
PMID:  11871909     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
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:
Nan Zhang; Joseph Vozzolo
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Mar 
Date Detail:
Created Date:  2002-03-01     Completed Date:  2002-04-25     Revised Date:  2003-11-03    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1703-4     Citation Subset:  -    
Affiliation:
Chemical Sciences, Wyeth-Ayerst Research, Pearl River, New York 10965 zhangn@war.wyeth.com
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