Formation of Five-Membered Cyclic Orthoesters from Tribromides with Participation of a Neighboring Carbonyl Group
DSpace at IIT Bombay
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Title |
Formation of Five-Membered Cyclic Orthoesters from Tribromides with Participation of a Neighboring Carbonyl Group
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Creator |
GURURAJA, GN
MOBIN, SM NAMBOOTHIRI, INN |
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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 |
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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.
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Publisher |
WILEY-BLACKWELL
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Date |
2012-06-26T04:49:58Z
2012-06-26T04:49:58Z 2011 |
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Type |
Article
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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 |
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Language |
English
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