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Paper | Regular issue | Vol 38, No. 10, 1994, pp.2277-2288
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6837
Photochemical Arylaminomethylation of the Pyrazine Derivatives having Electronegative Substituents

Mamoru Igarashi and Masaru Tada*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

5,6-Dichloropyrazine-2,3-dicarbonitrile (1), 2,3-dichloroquinoxaline (2), and pyrazine-2,3-dicarbonitrile (3) were photolyzed in acetonitrile in the presence of N-acyl-N-trimethylsilylmethylanilines (4 or 5). The photolysis is proposed to give an N-acylanilinomethyl radical by an electron transfer followed by the rupture of a trimethylsilyl cation. The anilinomethyl radical thus formed couples with the radical anion from the diazines to give the substitution products (6-9 and 11-14) of 1-3.