Author:
Peterson John R.,Do Hoang D.,Dunham Andrew J.
Abstract
The treatment of (E)-3,4-dimethoxycinnamic acid with ceric ammonium nitrate in trifluoroacetic acid afforded (E)-1,2-dimethoxy-4-nitro-5-(2-nitroethenyl)benzene in 79% yield. The unusual ipso substitution of the carboxylic acid moiety by a nitro functional center illustrated a new reaction manifold of cerium(IV). Six cinnamic acids were examined to ascertain the generality of the transformation. The bidentate nitrato structure of the metal salt is believed to account for the nitrating ability of this system.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
14 articles.
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