Ring opening of oxiranylmethyl and 3-methyl-3-oxetanylmethyl radicals

David Laurie*, Derek C. Nonhebel, Colin J. Suckling, John C. Walton

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Oxiranylmethyl and 3-methyl-3-oxetanylmethyl radicals were generated from the corresponding bromides and their rearrangements to allyloxyl and 2-methylprop-2-enyloxymethyl radicals respectively, were studied by kinetic EPR spectroscopy. The former radical was shown to ring open with a rate constant o≫ 4 x 108 s-1 at 25°C. The following kinetic parameters were measured for ring opening of the latter radical: k(25°C) = 8.9 x 102 s-1, log[A/s-1] = 13.97, E/kJ mol-1 = 63.3. Comparison of this data with that of related radicals supported the proposal that the transition state for β-scission of three-membered and four-membered cycloalkylmethyl radicals has dipolar character.

Original languageEnglish
Pages (from-to)5869-5872
Number of pages4
JournalTetrahedron
Volume49
Issue number26
DOIs
Publication statusPublished - 25 Jun 1993

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