Bicyclo[1.1.1]pent-1-yl: A tertiary alkyl radical with enhanced reactivity

Jeffrey T. Banks; Keith U. Ingold; Ernest W. Della; John C. Walton

doi:10.1016/0040-4039(96)01825-4

Bicyclo[1.1.1]pent-1-yl: A tertiary alkyl radical with enhanced reactivity

Jeffrey T. Banks, Keith U. Ingold, Ernest W. Della, John C. Walton^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Absolute rate constants for reactions of bicyclo[1.1.1]pent-1-yl radicals with α-methylstyrene (1.4 x 10⁷ M^-1s^-1) and 1,4-cyclohexadiene (4.6 x 10⁵ M-¹s^-1) at 25°C were measured by laser flash photolysis. This bridgehead radical is more reactive than tert-butyl which we attribute to its high s-character and the absence of steric shielding of the radical center.

Original language	English
Pages (from-to)	8059-8060
Number of pages	2
Journal	Tetrahedron Letters
Volume	37
Issue number	44
DOIs	https://doi.org/10.1016/0040-4039(96)01825-4
Publication status	Published - 28 Oct 1996

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abstract = "Absolute rate constants for reactions of bicyclo[1.1.1]pent-1-yl radicals with α-methylstyrene (1.4 x 107 M-1s-1) and 1,4-cyclohexadiene (4.6 x 105 M-1s-1) at 25°C were measured by laser flash photolysis. This bridgehead radical is more reactive than tert-butyl which we attribute to its high s-character and the absence of steric shielding of the radical center.",

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AU - Della, Ernest W.

AU - Walton, John C.

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AB - Absolute rate constants for reactions of bicyclo[1.1.1]pent-1-yl radicals with α-methylstyrene (1.4 x 107 M-1s-1) and 1,4-cyclohexadiene (4.6 x 105 M-1s-1) at 25°C were measured by laser flash photolysis. This bridgehead radical is more reactive than tert-butyl which we attribute to its high s-character and the absence of steric shielding of the radical center.

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Bicyclo[1.1.1]pent-1-yl: A tertiary alkyl radical with enhanced reactivity

Abstract

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