J. Peterson, H. D. Do, A. Dunham
Jul 1, 1988
Citations
0
Influential Citations
11
Citations
Journal
Canadian Journal of Chemistry
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.