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    
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.
Nan Zhang; Joseph Vozzolo
Related Documents :
15606099 - Tandem sonogashira coupling: an efficient tool for the synthesis of diarylalkynes.
20136159 - Palladium-catalyzed decarboxylative cross-coupling reaction between heteroaromatic carb...
20591679 - Development of chemical probes: toward the mode of action of a methylene-linked di(aryl...
15200329 - New and practical method for synthesis of 1- and 1,3-substituted xanthines.
20504029 - Efficient pallado-catalyzed c6-(het)arylation of imidazo[1,2-b][1,2,4,5]tetrazines unde...
11671639 - Synthesis of cyclo-2,2':4',4":2",2"':4"',4"":2"",2""':4""',4-sexipyridine.
24506229 - Trends in the electrochemical synthesis of h2o2: enhancing activity and selectivity by ...
12530909 - Nucleic acid related compounds. 118. nonaqueous diazotization of aminopurine derivative...
18835789 - Inducible and endothelial nitric oxide synthase expression in human atherogenesis: an i...
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:  -    
Chemical Sciences, Wyeth-Ayerst Research, Pearl River, New York 10965
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Facile synthesis of N-aryl pyrroles via Cu(II)-mediated cross coupling of electron deficient pyrrole...
Next Document:  Aromatic amination/imination approach to chiral benzimidazoles.