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Synthesis 1987; 1987(9): 834-835
DOI: 10.1055/s-1987-28093
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Stereoselective Synthesis of 2-Aryl-5-halo-2-pentenyl Methyl Sulfoxides and Sulfones

Michel Madesclaire* , Danielle Roche, André Boucherle, Alain Carpy
  • *Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, B. P. 38, F-63001 Clermont-Ferrand Cédex, France
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Publication Date:
12 September 2002 (online)

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Stereoselective formation of 2-aryl-5-halo-2-pentenyl methyl sulfoxides and sulfones is achieved by treatment of 2-aryl-2-cyclopropyl-2-hydroxyethyl methyl sulfoxides or sulfones, respectively, with hydrogen halides. In all cases, only the Z-isomer is isolated except for the 2-thiophenyl derivative which is designated as the E-isomer in accord with the Cahn sequence rule. Structures were determined by 1H-NMR spectrometry and for one product by X-ray crystallography.

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