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 ...
