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New Congeners of 1-Picryl-2-phenyl-2-(para-picramidophenyl)-diazenium Betaine whose Picramido Groups Are Replaced by 4-Cyano-2,6-dinitrophenyl Analogs

Covaci I.

Polish Journal of Chemistry

2001

Vol. 75, nr 10

1427-1440

By analogy with our previously described 1-picryl-2-phenyl-2-(para-picramidophenyl)- diazenium betaine (4a), three new congeners were synthesized in which either one, or the other, or both of the picryl groups have one 4-nitro group replaced by a cyano group. The spectral properties of these new compounds are described, and they prove that the cyanodinitrophenyl group behaves like a slightly less powerful electron-withdrawing group than a picryl group. The dipotassium salt of 1-picryl-2-phenyl-2-(4-picrylaminophenyl)- hydrazine (5a) forms a supramolecular complex, 13, with 18-crown-6 ether, which can be mono- or dialkylated with methyl iodide, resulting in a monomethyl and dimethyl derivative 14 and 15, respectively. The monomethyl derivative, 14, has the methyl attached to the diarylamino nitrogen atom, since oxidation by potassium permanganate converts it into a stable hydrazylic radical, 17.Abyproduct in the synthesis of betaine 4a, when an excess of DPPH is used over N-methoxypicramide, was proved to be 2-(4-methoxyphenyl)-2-phenyl-1-picrylhydrazine, 12. In order to avoid the formation of such byproducts and to allow simpler purification procedures, it is recommended to use equimolar ratios of reactants, in the presence of potassium permanganate.