Free radical cyclisation of unsaturated epoxides

✍ Scribed by Rosslyn C. Gash; Finlay MacCorquodale; John C. Walton

• Book ID: 104204801
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 407 KB
• Volume: 45
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89499-0

✦ Synopsis

Abstractz The e.s.r. spectra derived from 7-bromo-5.6epoxyheptene derivatives such OS epoxygeranyl bromide (7) showed that the main free radical intermediates were tetrahydr+ranybnethyl radicals (II). formed by ring opening of the epoxide and subsequent exocyclisation of the unsaturated alhoxyl radicals. The 7-oxabicyclo[2.2.I]heptanyl methyl radicals

(12) were also formed via a double cyclisation. Products derived from both these intermediates were isolatedfrom the reaction of ( 7) with tri-n-butyhin hydride.