1,4-Dienes from the nitration of 2,3- and 3,4-dimethylbenzonitriles and a 1,3-rearrangement of a nitro-group

Abstract

Reaction of 2,3- and 3,4-dimethylbenzonitriles with nitric acid in acetic anhydride gives 1,4-(nitroacetoxy-) adducts in which the nitro-group is attached to that nuclear carbon atom bearing a methyl group which is meta to the cyano-group; thermolysis of these adducts gives the original dimethylbenzonitrile, together with 2,3-dimethyl-5-nitrobenzonitrile and 3,4-dimethyl-5-nitrobenzonitrile, respectively.