Chakrabarti, Pinakpani and Venkatesan, Kailasam and Stanley Cameron, Theodore and Demi, Tursen and Shaw, Robert A (1981) Aromatic amines and their derivatives. Part 3. The synthesis and crystal structure of 4,4-NN-tetramethyl-NN-dinitroso-2,2-methylenedianiline. In: Perkin Transactions 1 (1). 206 -211.
full_text_12.pdf - Published Version
Restricted to Registered users only
Download (733Kb) | Request a copy
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.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Royal Society of Chemistry.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||01 Oct 2009 12:20|
|Last Modified:||19 Sep 2010 05:47|
Actions (login required)