Vicarious nucleophilic substitution of nitrobenzenes : Application of the reaction to 2-alkylnitrobenzenes

Article abstract of DOI:10.1080/00397919408020772

Vicarious nucleophilic substitution (VNS) by dichloroacetate and other reagents has been applied in good yield to various ortho-substituted nitrobenzenes including 2-nitrotoluene and 2-nitro ethylbenzene. For alkyl nitrobenzenes, ease of VNS increased para < ortho < meta and methyl < ethyl < iso-propyl. Formation of chlorine-free products upon VNS by methyl dichloro- acetate suggests the involvement of radical anions.

Full text of DOI:10.1080/00397919408020772

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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Vicarious Nucleophilic
Substitution of Nitrobenzenes
Gerath A. DeBoos a & David J. Milner b
a Process Technology Department , ZENECA plc ,
Hexagon House, Blackley, Manchester, M9 3DA, U. K.
b Specialties Research Centre , ZENECA plc ,
Hexagon House, Blackley, Manchester, M9 3DA, U. K.
Published online: 23 Sep 2006.
To cite this article: Gerath A. DeBoos & David J. Milner (1994) Vicarious Nucleophilic
Substitution of Nitrobenzenes, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 24:7, 965-976, DOI:
10.1080/00397919408020772
To link to this article: http://dx.doi.org/10.1080/00397919408020772
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