118510-00-2Relevant academic research and scientific papers
Cerium(IV)-induced nitration of cinnamic acids. Novel remote electrophilic substitution
Peterson, John R.,Do, Hoang D.,Dunham, Andrew J.
, p. 1670 - 1674 (2007/10/02)
The treatment of (E)-3,4-dimethoxycinnamic acid with ceric amonium nitrate in trifluoroacetic acid afforded (E)1,2-dimethoxy-4-nitro-5-(2-nitroethenyl)benzene in 79percent 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.
