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Communication | Regular issue | Vol 24, No. 11, 1986, pp.3027-3030
Published online, 1st January, 1970
DOI: 10.3987/R-1986-11-3027
Novel Ring Opening Reaction of 2-Aryl-1,2-benzisoselenazol-3(2H)-one with Thiols

Nobumasa Kamigata,* Mayumi Takata, Haruo Matsuyama, and Michio Kobayashi

*Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan


Reaction of 2-aryl-1,2-benzisoselenazol-3(2H)-one (1) with alkane- and arenethiols in dichloromethane at room temperature gives ring opening adducts, 2-alkyl- and 2-arylthioselenobenzanilides, respectively, probably via nucleophilic reaction of carbonyl oxygen of compound 1 to thiol hydrogen to give 3-hydroxy-2-aryl-1,2-benzisoselenazolium ion and thiolate anion, and subsequent nucleophilic attack on selenium atom by the resulting thiolate anion to generate the final ring opening product.