Journal of the Chemical Society. Perkin transactions I p. 1415 - 1421 (1989)
Update date:2022-07-30
Topics:
Adebayo, Adelaide T. O. M.
Bowman, W. Russell
Salt, W. G.
The anions of imidazole, benzimidazole, 5(6)-nitrobenzimidazole, and 5(and 6)-nitro-1H- and -2H-indazoles have been shown to undergo oxidative addition to the anion of 2-nitropropane (using potassium ferricyanide and sodium persulphate), and SRN1 reactions with Me2C(X)NO2 (X = Cl, Br, and NO2) to yield the corresponding 1-(1-methyl-1-nitroethyl) derivatives.The anions of 5(6)-nitrobenzimidazole and 5(6)-nitro-1H- and -2H-indazoles underwent reaction with p-nitrobenzyl chloride by a SRN1 and/or SN2 mechanism to yield the corresponding 1-(p-nitrobenzyl) derivatives.The ambident anions of 5- and 6-nitrobenzimidazole, 5-nitro-1H- and -2H-indazoles, and 6-nitro-1H- and -2H-indazoles gave ca. 50:50 mixtures of the N-1 alkylation products resulting from respective pairs of ambident anions.The 1-(1-methyl-1-nitroethyl) derivatives of benzimidazole and 5- and 6-nitro-1H-indazole underwent further substitution of the aliphatic nitro group with the respective diazole to yield 2,2-di(benzimidazol-1-yl)-, 2,2-di<5(and 6)-nitro-1H-indazol-1-yl>propanes.
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