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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/13905

Title: Formation of Five-Membered Cyclic Orthoesters from Tribromides with Participation of a Neighboring Carbonyl Group
Authors: GURURAJA, GN
MOBIN, SM
NAMBOOTHIRI, INN
Keywords: GAMMA-KETO ESTERS
RING-OPENING POLYMERIZATION
REGIOSELECTIVE PROTECTION
EFFICIENT SYNTHESIS
CATALYZED-REACTIONS
ENOL ETHERS
NITROALKANES
BUTENOLIDES
DERIVATIVES
CYCLIZATION
Issue Date: 2011
Publisher: WILEY-BLACKWELL
Citation: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,(11)2048-2052
Abstract: 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.
URI: http://dx.doi.org/10.1002/ejoc.201100042
http://dspace.library.iitb.ac.in/jspui/handle/100/13905
ISSN: 1434-193X
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