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