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Synthesis 1996; 1996(5): 637-640
DOI: 10.1055/s-1996-4268
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Selective Synthesis of cis-α,β-Unsaturated Sulfoxides and Sulfides by the Horner-Wittig Reaction with Bis(2,2,2-trifluoroethyl)phosphono Sulfoxides and Aromatic Aldehydes

Keisuki Kokin1 , Shuji Tsuboi, Jiro Motoyoshiya2 , Sadao Hayashi
  • 1Department of Materials Creation Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386, Japan, Fax +81(268)236214
  • 2Department of Materials Creation Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386, Japan, Fax +81(268)236214; E-mail jmotoyo@giptc.shinsu-u.ac.jp
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Publication Date:
31 December 2000 (online)

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cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.

Horner-Wittig reaction - bis(trifluoroethyl)phosphono sulfoxide - cis-selectivity - cis-α,β-unsaturated sulfoxide - cis-vinyl sulfide

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