Cerium (IV)-induced nitration of cinnamic acids. Novel remote electrophilic substitution

JR Peterson, HD Do…

文献索引：Peterson, John R.; Do, Hoang D.; Dunham, Andrew J. Canadian Journal of Chemistry, 1988 , vol. 66, p. 1670 - 1674

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被引用次数: 10

摘要

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 ...