Synthesis of Tetrasubstituted Ethylenic Compounds from a gem-Trichloroimidazole Derivative by Electron Transfer Reactions

Patrice Vanelle; Kamel Benakli; Luc Giraud; Michel P. Crozet

doi:10.1055/s-1999-2713

Synlett 1999; 1999(6): 801-803
DOI: 10.1055/s-1999-2713

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Synthesis of Tetrasubstituted Ethylenic Compounds from a gem-Trichloroimidazole Derivative by Electron Transfer Reactions

Patrice Vanelle^* , Kamel Benakli, Luc Giraud, Michel P. Crozet

^*Laboratoire de Chimie Organique, UMR 6517, Faculté de Pharmacie, 27 Bd Jean Moulin, 13385 Marseille Cedex 05, France; Fax +33 (4) 91 79 46 77; E-mail: patrice.vanelle@pharmacie.univ-mrs.fr

Abstract

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New 5-nitroimidazoles bearing a tetrasubstituted ethylenic double bond in 2-position were synthesized in high yields by the reaction of secondary nitronate anions with a new reductive alkylating agent, 1-methyl-2-trichloromethyl-5-nitroimidazole. Consecutive S_RN1 and E_RC1 mechanisms were followed in these processes.

5-nitroimidazoles - gem-trichloride - nitro compounds - phase-transfer - radical reaction

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