Journal of the Chemical Society. Perkin transactions I p. 403 - 407 (1981)
Update date:2022-08-04
Topics:
Mendoza, Javier de
Millan, Carles
Rull, Pedro
A synthesis of a 1,1'-bibenzimidazole (2; R = Me), through two successive heterocyclizations on 2,2'-azoaniline, is reported.Alternative routes to (2) by direct formation of the N-N bond from the appropriate N-substituted-benzimidazoles were unsuccessful.The dimer (2) shows great thermal and photochemical stability towards hydrogen abstraction and addition to olefins.Although the N-N bond can be easily cleaved by irradiation in ethanol, all attempts to detect the neutral radical benzimidazol-1-yl (1; R = Me) from (2) have been unsuccessful.Hydrogen abstraction by (1) is, however, observed with 1-iodobenzimidazole as the precursor.
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