Mn(III)-based reactions of alkenes and alkynes with thiols. An approach toward substituted 2,3-dihydro-1,4-oxathiins and simple route to (E)-vinyl sulfides

✍ Scribed by Van-Ha Nguyen; Hiroshi Nishino; Shougo Kajikawa; Kazu Kurosawa

• Book ID: 104208831
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 873 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00707-8

✦ Synopsis

The first example using manganese(Hi) acetate in the reaction of I,I--diarylethenes with ¢~-mercaptoketones was examined. A mixture of the ethenes and ct-mercaptoketones was treated with manganese(HI) acetate in acetic acid, affording cycloaddifon products in moderate yields, together with substituted products. The reaction may involve the formation of acarbocation and subsequenteyclization to give the substituted 2,3-dihydro-l,4--oxathiin 3. A similar reaction with thioglycolic acid gave 1,4oxathiolan-2-one 7. While thiyl radicals easily formed by manganese(HI) oxidation with ethanethiol or benzenethiol reacted with alkynes to give preferentially (E)-vinyl sulfides 1 0 in quantitative yields.