Reactions of Carbocations with π Nucleophiles: Polar Mechanism and No Outer Sphere Electron Transfer

Matthias Patz; Herbert Mayr; Junichi Maruta; Shunichi Fukuzumi

doi:10.1002/anie.199512251

Reactions of Carbocations with π Nucleophiles: Polar Mechanism and No Outer Sphere Electron Transfer

Matthias Patz, Herbert Mayr, Junichi Maruta, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

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48 Scopus citations

Abstract

Rate constants at least eight orders of magnitude greater than those calculated for the single electron transfer (SET) process are observed for the addition of R⁺ to π‐electron systems. Thus it is clear that in these reactions radical intermediates are generally not found, but that charge transfer is associated with the formation of the new CC σ bond. (Figure Presented.)

Original language	English
Pages (from-to)	1225-1227
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	34
Issue number	11
DOIs	https://doi.org/10.1002/anie.199512251
State	Published - 16 Jun 1995

Keywords

carbocations
electron transfer reactions
electrophilic additions
linear free energy relationships
reaction mechanisms

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10.1002/anie.199512251

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title = "Reactions of Carbocations with π Nucleophiles: Polar Mechanism and No Outer Sphere Electron Transfer",

abstract = "Rate constants at least eight orders of magnitude greater than those calculated for the single electron transfer (SET) process are observed for the addition of R+ to π‐electron systems. Thus it is clear that in these reactions radical intermediates are generally not found, but that charge transfer is associated with the formation of the new CC σ bond. (Figure Presented.)",

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author = "Matthias Patz and Herbert Mayr and Junichi Maruta and Shunichi Fukuzumi",

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T1 - Reactions of Carbocations with π Nucleophiles

T2 - Polar Mechanism and No Outer Sphere Electron Transfer

AU - Patz, Matthias

AU - Mayr, Herbert

AU - Maruta, Junichi

AU - Fukuzumi, Shunichi

PY - 1995/6/16

Y1 - 1995/6/16

N2 - Rate constants at least eight orders of magnitude greater than those calculated for the single electron transfer (SET) process are observed for the addition of R+ to π‐electron systems. Thus it is clear that in these reactions radical intermediates are generally not found, but that charge transfer is associated with the formation of the new CC σ bond. (Figure Presented.)

AB - Rate constants at least eight orders of magnitude greater than those calculated for the single electron transfer (SET) process are observed for the addition of R+ to π‐electron systems. Thus it is clear that in these reactions radical intermediates are generally not found, but that charge transfer is associated with the formation of the new CC σ bond. (Figure Presented.)

KW - carbocations

KW - electron transfer reactions

KW - electrophilic additions

KW - linear free energy relationships

KW - reaction mechanisms

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M3 - Article

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ER -

Reactions of Carbocations with π Nucleophiles: Polar Mechanism and No Outer Sphere Electron Transfer

Abstract

Keywords

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