An anomalous reaction of dimethyloxosulfonium methylide

✍ Scribed by Alexander G. Yurchenko; Natalie N. Melnik; Igor R. Likhotvorik

• Book ID: 104232915
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 133 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80472-x

✦ Synopsis

On treatment with dimethyloxosulfonium methylide in the presence of sodium methylsulfinylmethide, 3-methylenebicyclo[3.3. I] B? nane-7-one oxide undergoes an unusual transformation to 4,5-dimethylenetricyclo[4.3.1.0 9 ldecane-l-01. Diiethyloxosulfonium methyli& is an extremely important reagent for preparing oxiranesl or cyclopropanes.2 However, our attempt to obtain diepoxide 2 from 3-methylenebicyclo[3.3.l]nonane-'l-one oxide 1 was unsuccessful. Instead of the desired product, an unsaturated alcohol was formed3a to which the structure 4,5-dimethylenetricyclo[4.3. l.03j8]decane-l-01 3 was assigned by analysis of spectroscopic data.