Crystal and molecular structure of 4,N-dinitrobornan-2-imine (4,N-dinitrocamphorimine)

Abstract

The title compound (1) is shown from a single-crystal X-ray diffraction study to exist in a configuration with the N(1)–N(2) and C(2)–C(3) bonds syn. Crystals are orthorhombic, space group P2₁2₁2₁, with Z= 4 and a= 7.629(6), b= 7.729(5), c= 20.453(8); the structure was solved by direct methods and refined by full-matrix least squares to R 0.059 for 994 independent reflections. In the light of the configuration found for (1) we suggest that the previous mechanism for formation of nitro-imines be amended and propose a mechanism involving a radical pair intermediate.