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Experimental and computational studies have been performed in order to investigate an unusual carbon–carbon bond cleavage that occurs in the preparation of certain benzimidazole N-oxides from anilines. The key factor determining the outcome of the reaction was found to be the substituents on the amine functionality of the aniline.

Graphical abstract: Using experimental and computational approaches to probe an unusual carbon–carbon bond cleavage observed in the synthesis of benzimidazole N-oxides

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