Nitramines and nitramides. Part XVII. Reactions with dicyclohexylcarbodi-imide

Abstract

The reaction of dicyclohexylcarbodi-imide with aliphatic primary nitramines (RNH·NO₂) yielded NN′-dicyclohexylurea and nitrous oxide, together with variable proportions of RN:NO₂R, R₂N·NO₂, and the olefin which might be derived from the alkyl group R. 2,4,6-Tribromophenylnitramine gave the urea and a tar, from which 1,3,5-tribromobenzene was obtained by sublimation.

Primary nitro-carbamates (RO₂C·NH·NO₂; R = Me or Et) yielded stable addition compounds which we formulate as C₆H₁₁N(CO₂R)·C(NH·NO₂):NC₆H₁₁, and which could be hydrolysed to NN′-dicyclohexyl-N″-nitroguanidine; but concurrent reactions took place so that, in the case of nitrourethane (R = Et), the dicyclohexylurea, nitrous oxide, carbon dioxide, and ethylene were also identified as products. A few reactions with other nitramines and carbodi-imides are reported briefly.