The Journal of Organic Chemistry

Alkyl nitrate nitration of active methylene compounds. XI. Nitration of toluenes. Facile preparation of stilbenes

H Feuer, H Friedman

Index: Feuer,H.; Friedman,H. Journal of Organic Chemistry, 1975 , vol. 40, # 2 p. 187 - 190

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Citation Number: 16

Abstract

The alkyl nitrate nitration of toluenes substituted in the ortho or para position with an electron- withdrawing group gives the corresponding a-nitrotoluenes in yields of about 40-55%. The reaction is successful with o-and p-tolunitriles, N, N-dimethyl-p-toluenesulfonamide, phenyl p-tolyl sulfone, 4-methylbenzophenone, and even such a weak acid as diphenylmethane. The reaction is unsuccessful with 0-and pN, N-dimethyltoluamides, which are converted ...