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Paper | Regular issue | Vol 63, No. 5, 2004, pp.1077-1081
Published online, 26th March, 2004
DOI: 10.3987/COM-04-10010
Organic Reactions in Ionic Liquids: A Simple Highly Regioselective or Regiospecific Substitutions of Benzotriazole

Zhang-Gao Le, Zhen-Chu Chen,* Yi Hu, and Qin-Guo Zheng

*Department of Chemistry, Zhejiang Universityh (XiXi Campus), Hangzhou, Zhejiang 310028, China

Abstract

In the absence of any added base in ionic liquids [Bmim][BF4], 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.