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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 53, 1990 - Issue 1-4
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Original Articles

NOVEL HALOGENATION OF THIOPHENES WITH BENZENESELENINYL CHLORIDE AND ALUMINUM HALIDE

Nobumasa Kamigata Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Fukazawa, Setagaya-ku, Tokyo, 158, Japan
,
Takashi Suzuki Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Fukazawa, Setagaya-ku, Tokyo, 158, Japan
,
Masato Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Fukazawa, Setagaya-ku, Tokyo, 158, Japan
&
Yoshida Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Fukazawa, Setagaya-ku, Tokyo, 158, Japan
Pages 29-35 | Received 24 Oct 1989, Published online: 23 Sep 2006
 
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Abstract

In the presence of aluminum halide, benzeneseleninyl chloride is an efficient Regioselective halogenating reagent for heterocyclic compounds such as thiophene, 2methylthiophene. 3-methylthiophene, 2,5-dimethylthiophene, and furan. In the case of pyrrole, no halogenated product was obtained. A plausible reaction mechanism involving a positive halogen intermediate is proposed.

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