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Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

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Title Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO
 
Creator MANNA, S
JANA, S
SABOO, T
MAJI, A
MAITI, D
 
Subject ARYLBORONIC ACIDS
NITROOLEFINS
NITROALKENES
ALKENES
OLEFINS
NITROSTYRENES
HYDROGENATION
NITROARENES
DERIVATIVES
CONVENIENT
 
Description Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from alpha,beta-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. alpha,beta-Unsaturated carboxylic acids bearing beta-aromatic and beta-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-15T16:39:41Z
2014-10-15T16:39:41Z
2013
 
Type Article
 
Identifier CHEMICAL COMMUNICATIONS, 49(46)5286-5288
http://dx.doi.org/10.1039/c3cc41576g
http://dspace.library.iitb.ac.in/jspui/handle/100/15232
 
Language en