Issue 0, 1981

Aromatic amines and their derivatives. Part 3. The synthesis and crystal structure of 4,4′-NN′-tetramethyl-NN′-dinitroso-2,2′-methylenedianiline

Abstract

The synthesis of 4,4′,N,N′-tetramethyl-NN′-dinitroso-2,2′-methylenedianiline (1) by the route p-MeC6H4NH2+ HCHO + OH(p-MeC6H4NMe)2CH2(7b); (7b)+ acid at 70 °C 4,N-dimethyl-6-(N-methyl-p-toluidinomethyl)aniline (4b); (4b)+ acid at 130 °C 4,4′,NN′-tetramethyl-2,2′-methylenedianiline (3b); (3b)+ HNO2(1), is described. Aspects of the 1H n.m.r. spectra of the above and related compounds are discussed. A crystal-structure analysis of compound (1) shows one of the N-nitroso-groups to be disordered with the endo-form being in preponderance (4 : 1) over the exo-form. The other N-nitroso-group is exclusively exo in the solid state. There is little or no resonance between the benzene ring and the nitroso-group attached to the ring, the two groups being almost perpendicular to each other. In one of the N-nitroso-groups, the nitrogen atom deviates significantly from the plane of the benzene ring to which it is attached. Both amide nitrogen atoms show some pyramidal character.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 206-211

Aromatic amines and their derivatives. Part 3. The synthesis and crystal structure of 4,4′-NN′-tetramethyl-NN′-dinitroso-2,2′-methylenedianiline

P. Chakrabarti, K. Venkatesan, T. S. Cameron, T. Demir and R. A. Shaw, J. Chem. Soc., Perkin Trans. 1, 1981, 206 DOI: 10.1039/P19810000206

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