The spiropentyl radical and some homolytic reactions of spiropentane

Alan J. Kennedy, John C. Walton*, Keith U. Ingold

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Spiropentyl radical was generated by hydrogen abstraction from spiropentane by t-butoxyl radical and its e.s.r. spectrum obtained. The experimental e.s.r. parameters were compared with computational results obtained using semi-empirical SCF MO methods. The spiropentyl radicals do not undergo β-scission in the observable temperature range (T < 380 K). The main process in the halogenation of spiropentane at 293 K in CCl4 solution involves SH2 attack by the halogen atom to give 1-(halogenomethyl) cyclopropylmethyl radicals. The β-scission of these latter radicals has been investigated by e.s.r. spectroscopy and by the reduction of 1,1-bisbromomethyl-cyclopropane with tri-n-butyltin hydride.

Original languageEnglish
Pages (from-to)751-757
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number6
Publication statusPublished - 1 Dec 1982

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