The spiropentyl radical and some homolytic reactions of spiropentane

Alan J. Kennedy; John C. Walton; Keith U. Ingold

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 journal › Article › peer-review

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 S_H2 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 language	English
Pages (from-to)	751-757
Number of pages	7
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	6
Publication status	Published - 1 Dec 1982

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title = "The spiropentyl radical and some homolytic reactions of spiropentane",

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.",

author = "Kennedy, \{Alan J.\} and Walton, \{John C.\} and Ingold, \{Keith U.\}",

year = "1982",

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journal = "Journal of the Chemical Society, Perkin Transactions 2",

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T1 - The spiropentyl radical and some homolytic reactions of spiropentane

AU - Kennedy, Alan J.

AU - Walton, John C.

AU - Ingold, Keith U.

PY - 1982/12/1

Y1 - 1982/12/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/37049100897

M3 - Article

AN - SCOPUS:37049100897

SN - 1472-779X

SP - 751

EP - 757

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

IS - 6

ER -

The spiropentyl radical and some homolytic reactions of spiropentane

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