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Formation of Five-Membered Cyclic Orthoesters from Tribromides with Participation of a Neighboring Carbonyl Group

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Title Formation of Five-Membered Cyclic Orthoesters from Tribromides with Participation of a Neighboring Carbonyl Group
 
Creator GURURAJA, GN
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject GAMMA-KETO ESTERS
RING-OPENING POLYMERIZATION
REGIOSELECTIVE PROTECTION
EFFICIENT SYNTHESIS
CATALYZED-REACTIONS
ENOL ETHERS
NITROALKANES
BUTENOLIDES
DERIVATIVES
CYCLIZATION
Ketones
Hydrolysis
Neighboring-group effects
Orthoesters
Heterocycles
 
Description The Mg-mediated conjugate addition of bromoform to enones followed by alcoholysis of the resulting keto tribromides proceeds through an unusual course, affording cyclic orthoester (dihydrofuran) intermediates under neutral workup conditions. However, acid workup of the reaction mixture or treatment of the isolated dihydrofurans with acid provides the expected but synthetically useful gamma-keto esters. The intermediacy of dihydrofurans in the one-pot transformation of keto tribromides into gamma-keto esters provides evidence for the active participation of the neighboring carbonyl group in the alcoholysis of the tribromide moiety.
 
Publisher WILEY-BLACKWELL
 
Date 2012-06-26T04:49:58Z
2012-06-26T04:49:58Z
2011
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,(11)2048-2052
1434-193X
http://dx.doi.org/10.1002/ejoc.201100042
http://dspace.library.iitb.ac.in/jspui/handle/100/13905
 
Language English