Substituent Effect on the Electrochemical Oxidation of Trityl Anions

Shelton Bank; Clifford L. Ehrlich; Jon A. Zubieta

doi:10.1021/jo01323a020

Substituent Effect on the Electrochemical Oxidation of Trityl Anions

Shelton Bank, Clifford L. Ehrlich, Jon A. Zubieta

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

26 Scopus citations

Abstract

The reversible one-electron oxidations of triaryl anions and the irreversible second oxidative processes were examined for a series of sequentially substituted p-methyl anions. The cycle voltammograms of the lithium salts prepared in dimethoxyethane reveal that each of the potentials depends upon the substituent in the para positions. The relative effect of substituent on the stability of the several species is compared with other known measurements. Additionally, the relationship between carbanion stability and reduction potential is discussed.

Original language	English (US)
Pages (from-to)	1454-1458
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	44
Issue number	9
DOIs	https://doi.org/10.1021/jo01323a020
State	Published - 1979
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo01323a020

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title = "Substituent Effect on the Electrochemical Oxidation of Trityl Anions",

abstract = "The reversible one-electron oxidations of triaryl anions and the irreversible second oxidative processes were examined for a series of sequentially substituted p-methyl anions. The cycle voltammograms of the lithium salts prepared in dimethoxyethane reveal that each of the potentials depends upon the substituent in the para positions. The relative effect of substituent on the stability of the several species is compared with other known measurements. Additionally, the relationship between carbanion stability and reduction potential is discussed.",

author = "Shelton Bank and Ehrlich, {Clifford L.} and Zubieta, {Jon A.}",

year = "1979",

doi = "10.1021/jo01323a020",

language = "English (US)",

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pages = "1454--1458",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Substituent Effect on the Electrochemical Oxidation of Trityl Anions

AU - Bank, Shelton

AU - Ehrlich, Clifford L.

AU - Zubieta, Jon A.

PY - 1979

Y1 - 1979

N2 - The reversible one-electron oxidations of triaryl anions and the irreversible second oxidative processes were examined for a series of sequentially substituted p-methyl anions. The cycle voltammograms of the lithium salts prepared in dimethoxyethane reveal that each of the potentials depends upon the substituent in the para positions. The relative effect of substituent on the stability of the several species is compared with other known measurements. Additionally, the relationship between carbanion stability and reduction potential is discussed.

AB - The reversible one-electron oxidations of triaryl anions and the irreversible second oxidative processes were examined for a series of sequentially substituted p-methyl anions. The cycle voltammograms of the lithium salts prepared in dimethoxyethane reveal that each of the potentials depends upon the substituent in the para positions. The relative effect of substituent on the stability of the several species is compared with other known measurements. Additionally, the relationship between carbanion stability and reduction potential is discussed.

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ER -

Substituent Effect on the Electrochemical Oxidation of Trityl Anions

Abstract

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