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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3848

Title: Facile Synthesis of beta-Tribromomethyl and Dibromomethylenated Nitroalkanes via Conjugate Addition of Bromoform to Nitroalkenes
Authors: SAHU, B
GURURAJA, GN
MOBIN, SM
NAMBOOTHIRI, INN
Keywords: electron-poor alkenes
nucleophilic-substitution
regioselective synthesis
rearrangement
haloforms
dihalocarbenes
derivatives
generation
catalyst
hydrogen
Issue Date: 2009
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 74(6), 2601-2604
Abstract: 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.
URI: http://dx.doi.org/10.1021/jo802274q
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3848
http://hdl.handle.net/10054/3848
ISSN: 0022-3263
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