A simple method for the synthesis of γ-functionalized vinyl and allyl sulfones

✍ Scribed by Carmen Nájera; Alfonso Pérez-Pinar; JoséM. Sansano

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 1020 KB
• Volume: 47
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86563-7

✦ Synopsis

The synthesis of y-functionalized vinyl sulfonea 3 have been carried out directly starting from dibromldes 2 derived from ally1 sulfones 1 by reaction with different nucleophiles. The process is stereoselective affording compounds 3 with E configuration except in the case of methallylic derivatives. The regioisomeric y-functional&d ally1 sulfones 4 were obtained from dibromidea 2 or from vinyl sulfones 3, wlth Z configuration, except when triphe-nylphosphine was used as nucleophile, in this case the corresponding Q-vinylphosphonium bromide 4al was obtained. Vinyl and ally1 sulfones are the most synthetically useful sulfones in Organic Chemistry.' The