PDF herunterladen
Synthesis 1996; 1996(5): 637-640
DOI: 10.1055/s-1996-4268
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

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