Effect of halogens on the activity of halonitrobenzenes in reactions with carbanions

On the basis of competition experiments using a model VNS reaction of chloromethyl phenyl sulfone with halonitrobenzenes it was shown that halogen substituents activate electron-deficient nitroarenes for the addition of carbanions whereas they protect the positions they occupy against the addition....

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 11; pp. 2577 - 2581
Main Authors Makosza, M, Lobanova, O, Kwast, A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 08.03.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
VICARIOUS NUCLEOPHILIC-SUBSTITUTION
AROMATIC NITRO-COMPOUNDS
HYDROGEN
NITROARENES
halonitrobenzenes
MECHANISM
carbanions
ORIENTATION
COMPETITION
vicarious substitution
COMPLEXES
ORGANIC-ANIONS
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Summary:On the basis of competition experiments using a model VNS reaction of chloromethyl phenyl sulfone with halonitrobenzenes it was shown that halogen substituents activate electron-deficient nitroarenes for the addition of carbanions whereas they protect the positions they occupy against the addition. (C) 2004 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.01.038