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Paper | Regular issue | Vol 78, No. 9, 2009, pp.2315-2324
Published online, 1st June, 2009
DOI: 10.3987/COM-09-11734
Reactions of Radicals Generated from 1-Ethyl-1,4-diazinium-salts: Addition to the C-C Triple Bond versus Dimerization

Gennadiy L. Rusinov,* Egor V. Verbitskiy, Pavel A. Slepukhin, Olga N. Zabelina, Mikhail I. Kodess, Marina A. Ezhikova, Valeriy N. Charushin, and Oleg N. Chupakhin

*I. Postovsky Institute of Organic Synthesis, 620041 Ekaterinburg, GSP-147, S. Kovalevskoy Str., 22, Russia

Abstract

Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into [2,2]bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyrazinyl radicals can also be involved into the addition reaction on the C-C triple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1′,2′-dihydropyrazinyl-2′)-2-iodoethenes have been proved by 1H and 13C NMR spectroscopy and X-ray analysis.