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Metal-free reductive cleavage of C-O sigma-bonds in acyloin derivatives by an organic neutral super-electron-donor.
MedLine Citation:
PMID:  19845372     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Neutral organic electron-donor 7, formally a pyridinylidene carbene dimer, effects reductive cleavage of C-O sigma-bonds in acyloin derivatives Ar(CO)CRR'OX (X = OAc, OPiv, OBz, OMs) and this represents the first cleavage of C-O sigma-bonds by a neutral organic electron-donor. The methodology is applicable to a large array of substrates and the reduced counterparts were isolated in good to excellent yields. For certain substrates, donor 7 behaves as a base, effecting condensation reactions with some acetate ester derivatives of acyloins, leading to butenolides. The variation in reactivity among the different substrates was rationalized.
Authors:
Sylvain P Y Cutulic; Neil J Findlay; Sheng-Ze Zhou; Ewan J T Chrystal; John A Murphy
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Nov 
Date Detail:
Created Date:  2009-11-13     Completed Date:  2010-01-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8713-8     Citation Subset:  -    
Affiliation:
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow, G1 1XL, United Kingdom.
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