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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/11784

Title: Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes
Authors: SHANBHAG, P
NAREDDY, PR
DADWAL, M
MOBIN, SM
NAMBOOTHIRI, INN
Keywords: baylis-hillman reaction
pauson-khand reaction
alpha,beta-unsaturated nitro-compounds
dabco-catalyzed dimerization
conjugated nitroalkenes
anticancer activity
michael cycloisomerization
activated olefins
acrylic compounds
esters
Issue Date: 2010
Publisher: ROYAL SOC CHEMISTRY
Citation: ORGANIC & BIOMOLECULAR CHEMISTRY, 8(21), 4867-4873
Abstract: Reaction of nitroalkenes or nitrodienes with methyl vinyl ketone (MVK) or acrylate in the presence of the imidazole-LiCl catalyst system provides Rauhut-Currier (vinylogous Morita-Baylis-Hillman) adducts in moderate yield. Under similar conditions (imidazole-hydroquinone), nitroalkenes and nitrodienes undergo self-dimerization to afford the Rauhut-Currier adducts in varying yields. An alternative self-dimerization-nitro group elimination pathway in the presence tricyclohexylphosphine was observed with heteroaromatic nitroalkenes. A synthetically useful one-pot two step transformation of Rauhut-Currier adducts of nitroalkenes with MVK to 2,3-disubstituted cyclopentenones is also described.
URI: http://dx.doi.org/10.1039/c0ob00062k
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11784
http://hdl.handle.net/10054/11784
ISSN: 1477-0520
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