Science of Synthesis

Tang, Y.; Sun, X.-L., Science of Synthesis, (2008) 39, 1088.

Selenolane dibromides are good electrophilic reagents and can react with alkenes such as cyclohexene, methylene- and 3-cyano(methylene)cyclobutane, norbornene, and nor­bornadiene in acetonitrile to afford cyclic trialkylselenonium salts in 50–90% yield (‌Scheme 11‌).[‌23‌] This method provides easy access to β-haloselenonium salts. The reaction proceeds stereo- and regiospecifically according to Markovnikov's rule. Thus selenonium salts bearing a tertiary or quaternary carbon atom on the selenium atom, which are usually difficult to prepare by reaction of cyclic selenides with alkyl halides, are obtained.

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References