Free radical cyclisation of unsaturated epoxides

Rosslyn C. Gash*, Finlay MacCorquodale, John C. Walton

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The e.s.r. spectra derived from 7-bromo-5,6-epoxyheptene derivatives such as epoxygeranyl bromide (7) showed that the main free radical intermediates were tetrahydrofuranylmethyl radicals (11), formed by ring opening of the epoxide and subsequent exocyclisation of the unsaturated alkoxyl radicals. The 7-oxabicyclo[2.2.1]heptanyl methyl radicals (12) were also formed via a double cyclisation. Products derived from both these intermediates were isolated from the reaction of (7) with tri-n-butyltin hydride.

Original languageEnglish
Pages (from-to)5531-5538
Number of pages8
JournalTetrahedron
Volume45
Issue number17
DOIs
Publication statusPublished - 1 Jan 1989

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