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Paper | Regular issue | Vol 36, No. 5, 1993, pp.1127-1138
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6312
Nucleophilic Radical Substitution of Polychloroazines

Nobuhiro Kanomata, 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

Polychloroazines (1-6) are susceptible to homolytic chlorine substitution by alkyl radicals. In general, the chlorine at the ortho-position to the ring nitrogen is readily replaced by an alkyl radical like adamantyl and tert-butyl. However, the chlorine at the C2-position of pyrimidine did not show any sign of the radical substitution. The reactivity decreases in the order of adamantyl, tert-butyl, and isopropyl radicals.