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

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.",

author = "Banks, \{Jeffrey T.\} and Ingold, \{Keith U.\} and Della, \{Ernest W.\} and Walton, \{John C.\}",

year = "1996",

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doi = "10.1016/0040-4039(96)01825-4",

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T2 - A tertiary alkyl radical with enhanced reactivity

AU - Banks, Jeffrey T.

AU - Ingold, Keith U.

AU - Della, Ernest W.

AU - Walton, John C.

PY - 1996/10/28

Y1 - 1996/10/28

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/0030605107

U2 - 10.1016/0040-4039(96)01825-4

DO - 10.1016/0040-4039(96)01825-4

M3 - Article

AN - SCOPUS:0030605107

SN - 0040-4039

VL - 37

SP - 8059

EP - 8060

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

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

Abstract

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