BY-PRODUCTS IN THE REARRANGEMENT OF N-METHYL-N-PHENYLNITRAMINE

N-Methyl-N-phenylnitramine was rearranged in the aqueous dioxane - sul phuric acid mixture to 2-nitro- and 4-nitro-N-methylanilines. The isom er ratio was independent of the acidity within the range of -0.3 > H-o > -2.8. Some by-products were isolated and identified e.g. N-methyl-N -nitrosoaniline, its 2-nitro and 4-nitro derivatives, nitrosobenzene a nd 4',4 ''-Bis-(N-methylamino)-3'.3 ''-dinitrodiphenylmethane. The mec hanism of the nitramine rearrangement is discussed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.