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Short Paper | Regular issue | Vol 89, No. 2, 2014, pp.473-480
Published online, 26th December, 2013
DOI: 10.3987/COM-13-12888
Reaction of Fenchone Hydrazone with Diselenium Dibromide: Novel Formation of Bicyclic Diselenide

Kentaro Okuma,* Kazunori Munakata, Hiroyuki Matsui, Noriyoshi Nagahora, and Kosei Shioji

*Department of Chemistry, Faculty of Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

Bicyclic diselenane containing a norbornane skeleton was synthesized by the reaction of fenchone hydrazone with Se2Br2. Initially formed selenofenchone further reacted with another molar amount of Se2Br2 to afford Wagner-Meerwein rearranged diselenane. Camphor hydrazone also reacted with Se2Br2 to afford the corresponding diselenane, whereas no rearranged product was formed.