Nitric acid oxidation of polyalkylbenzenes

EW Crandall, R Beasley, LL Lambing…

Index: Crandall,E.W. et al. Journal of Organic Chemistry, 1967 , vol. 32, p. 134 - 136

Full Text: HTML

Citation Number: 16

Abstract

2-Substituted p-xylenes on oxidation with nitric acid gave both isomeric toluic acids with the 3-substituted acid predominating. Ease of oxidation of a methyl group meta to the substituent is in the order Br> C1> NO2> F, that in theortho position is C1> Br> F> NO2, while the order at the para position is Br> C1> F> NO2. The effect appears to be inductive rather than mesomeric.

Related Articles:

Enantiospecific synthesis of SB 214857, a potent, orally active, nonpeptide fibrinogen receptor antagonist

[Miller, William H.; Ku, Thomas W.; Ali, Fadia E.; Bondinell, William E.; Calvo, Raul R.; Davis, Larry D.; Erhard, Karl F.; Hall, Leon B.; Huffman, William F.; Keenan, Richard M.; Kwon, Chet; Newlander, Kenneth A.; Ross, Stephen T.; Samanen, James M.; Takata, Dennis T.; Yuan, Chuan-Kui Tetrahedron Letters, 1995 , vol. 36, # 52 p. 9433 - 9436]

The first regioselective metalation and functionalization of unprotected 4-halobenzoic acids

[Gohier, Frederic; Castanet, Anne-Sophie; Mortier, Jacques Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1501 - 1504]

More Articles...