16098-49-0Relevant academic research and scientific papers
DUAL REACTIVITY OF CONJUGATED DIANIONS OF DINITRO COMPOUNDS. REACTIONS WITH BROMINE AND DIAZONIUM SALTS
Lipina, E. S.,Stepanov, N. D.,Bagal, I. L.,Bodina, R. I.,Perekalin, V. V.
, p. 2059 - 2067 (2007/10/02)
In contrast to all known anions of nitro compounds and other CH acids, the conjugated dianions of dinitro compounds react with diazonium salts with release of nitrogen and the formation of covalent products.On the basis of an analysis of the spectral data the products were assigned the structure of previously unknown bis-O-aryl nitronic esters.By redoximetric titration with bromine and diazonium salt it was established that the investigated anions have low oxidation potentials compared with unconjugated anions of nitro compounds and are extremely mild nucleophiles.On the basis of thermodynamic considerations it was demonstrated that the products from covalent O-addition of the diazo cations and the products from oxidation-reduction transformation during reaction with halogens can be formed from the conjugated dianions of the dinitro compounds.The dual reactivity of the anions of the nitro compounds was evaluated in terms of PMO theory.
