In the absence of any added base in ionic liquids [Bmim][BF 4 ], benzotriazole replaces the halogen atom of an α-halogenated ketone or α-halogenated carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer, and 1-chloro-2,4-dinitrobenzene reacted similarly with benzotriazole to afford the N-1-substituted benzotriazole in a good yield.Alkyl halides reacted regioselectively to afford the N-1-alkylbenzotriazole in ratios of more than 15 to 1 over the N-2-isomer.
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Chen et al. (2004) studied this question.
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