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Facile Synthesis of beta-Tribromomethyl and Dibromomethylenated Nitroalkanes via Conjugate Addition of Bromoform to Nitroalkenes

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Title Facile Synthesis of beta-Tribromomethyl and Dibromomethylenated Nitroalkanes via Conjugate Addition of Bromoform to Nitroalkenes
 
Creator SAHU, B
GURURAJA, GN
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject electron-poor alkenes
nucleophilic-substitution
regioselective synthesis
rearrangement
haloforms
dihalocarbenes
derivatives
generation
catalyst
hydrogen
 
Description Addition of bromoform to conjugated nitroalkenes in the presence of Mg provided beta-tribromomethyl nitroalkanes in good to excellent yields and diastereoselectivity. These novel Michael adducts, formed under radical conditions, underwent elimination of HBr in the same pot under reflux to afford beta-dibromomethylenated nitroalkanes in good yield. Alternatively, a one-pot high yielding synthesis of the dibromides was possible under anionic conditions via LDA mediated addition of bromoform to nitroalkenes.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T03:32:39Z
2011-12-26T12:47:32Z
2011-12-27T05:36:04Z
2011-07-14T03:32:39Z
2011-12-26T12:47:32Z
2011-12-27T05:36:04Z
2009
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 74(6), 2601-2604
0022-3263
http://dx.doi.org/10.1021/jo802274q
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3848
http://hdl.handle.net/10054/3848
 
Language en