Direct synthesis of sulfines by oxidation of enethiolizable thioketones

✍ Scribed by Anne Marie Le Nocher; Patrick Metzner

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 216 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)74874-x

✦ Synopsis

Reactlon of enethlohzable thloketones 2 with one equivalent of metachloroperoxybenzolc acid affords quantltatlvely the corresponding E sulfines 1 In contrast to hterature expectations, direct synthesis of allphatlc sulfines by oxldatlon of thlocarbonyl compounds 1s thus possible, no dlvmyl &sulfide 4 has been formed Sulfines 1 are reactive heterocumulenes, for which a vanety of synthetic routes has been developed (l-5) Direct oxldatlon of thlocarbonyl compounds 2 1s limited to aromatlc, non enethlohzable and a-unsaturated cases (2, 6-11) Our group has recently reported (12) that reactlon of enethlohzable dlthloesters with meta-chloroperoxybenzolc acid (mCPBA) grves the correspondmg sulfines, whose stablhtles have been studied In the case of thloketones, the literature predicts (2, 5, 13, 14) the formatlon of dlvmyl dlsulfides 4 Intngued by these expectations and needing ahphatlc sulfines for synthetic purposes, we revlslted this oxldatlon