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Paper | Regular issue | Vol 51, No. 3, 1999, pp.557-565
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8402
Competition between C- and O-Alkylation Reactions in 5-Nitroimidazole Series: Influence of Nucleophile

Kamel Benakli, Mustapha Kaafarani, Michel P. Crozet, and Patrice Vanelle*

*Laboratoire de Chimie Organique, Faculté de Pharmacie, Université de la Méditerranée, 27, Boulevard Jean Moulin, 13385 Marseille Cedex 05, France

Abstract

The new reductive alkylating agent, 2-(4-chloromethylstyryl)-1-methyl-5-nitro-1H-imidazole gives exclusively O-alkylation with 2-nitropropane anion. The electron-transfer C-alkylation is observed with the anions of ethyl 2-nitro-propionate and dialkyl α-substituted malonates. The competition between C- and O-alkylation reactions depends on the nature of the nucleophile because of the low rate of decomposition of the radical anion of the alkylating agent.