Carbocation lifetimes that are independent of carbocation stability: The reaction of α-substituted 4-methoxybenzyl carbocations

Tina L. Amyes; John P. Richard

doi:10.1039/C39910000200

Carbocation lifetimes that are independent of carbocation stability: The reaction of α-substituted 4-methoxybenzyl carbocations

Chemistry

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Abstract

The α-methoxy-4-methoxybenzyl carbocation reacts with the solvent trifluoroethanol-water (50: 50 v/v) with a rate constant k_s = 3 × 10⁷ s^-1; k_s increases by less than twofold when the carbocation is destabilised by replacement of the strongly electron donating α-OMe substituent by the strongly electron withdrawing α-CF₃ substituent.

Original language	English
Pages (from-to)	200-202
Number of pages	3
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	3
DOIs	https://doi.org/10.1039/C39910000200
State	Published - 1991

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@article{e898bfcd9c96401883cc52fa864ea278,

title = "Carbocation lifetimes that are independent of carbocation stability: The reaction of α-substituted 4-methoxybenzyl carbocations",

abstract = "The α-methoxy-4-methoxybenzyl carbocation reacts with the solvent trifluoroethanol-water (50: 50 v/v) with a rate constant ks = 3 × 107 s-1; ks increases by less than twofold when the carbocation is destabilised by replacement of the strongly electron donating α-OMe substituent by the strongly electron withdrawing α-CF3 substituent.",

author = "Amyes, \{Tina L.\} and Richard, \{John P.\}",

year = "1991",

doi = "10.1039/C39910000200",

language = "English",

pages = "200--202",

journal = "Journal of the Chemical Society D: Chemical Communications",

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publisher = "Chemical Society",

number = "3",

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T1 - Carbocation lifetimes that are independent of carbocation stability

T2 - The reaction of α-substituted 4-methoxybenzyl carbocations

AU - Amyes, Tina L.

AU - Richard, John P.

PY - 1991

Y1 - 1991

N2 - The α-methoxy-4-methoxybenzyl carbocation reacts with the solvent trifluoroethanol-water (50: 50 v/v) with a rate constant ks = 3 × 107 s-1; ks increases by less than twofold when the carbocation is destabilised by replacement of the strongly electron donating α-OMe substituent by the strongly electron withdrawing α-CF3 substituent.

AB - The α-methoxy-4-methoxybenzyl carbocation reacts with the solvent trifluoroethanol-water (50: 50 v/v) with a rate constant ks = 3 × 107 s-1; ks increases by less than twofold when the carbocation is destabilised by replacement of the strongly electron donating α-OMe substituent by the strongly electron withdrawing α-CF3 substituent.

UR - https://www.scopus.com/pages/publications/37049081899

U2 - 10.1039/C39910000200

DO - 10.1039/C39910000200

M3 - Article

AN - SCOPUS:37049081899

SN - 0022-4936

SP - 200

EP - 202

JO - Journal of the Chemical Society D: Chemical Communications

JF - Journal of the Chemical Society D: Chemical Communications

IS - 3

ER -

Carbocation lifetimes that are independent of carbocation stability: The reaction of α-substituted 4-methoxybenzyl carbocations

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