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Synthesis 1992; 1992(4): 377-379
DOI: 10.1055/s-1992-26116
short paper
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A Convenient Procedure for the Preparation of Organic Selenides

Makoto Sakakibara* , Kazuhiro Katsumata, Yoshihiko Watanabe, Takeshi Toru, Yoshio Ueno
  • *Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466, Japan
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Publication Date:
17 September 2002 (online)

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Treatment of diphenyl diselenide with tributylphosphine in an alkaline medium forms phenylselenolate ion which converts alkyl halides, α,β-unsaturated ketones, and epoxides into alkyl selenides, (phenylseleno)alkenones, and β-(phenylseleno) alkanols, respectively, in high yield. Selenation of 3α-bromocholestane gives 3β-(phenylseleno)cholestane with complete inversion of the configuration.