Substituent Effect on the Electrochemical Oxidation of Trityl Anions. 2. Effect of an Electron-Withdrawing Group

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

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The reversible one-electron oxidations of triarylmethyl anions and the irreversible second oxidative processes were examined for a series of sequentially substituted p-trimethylsilyl anions. The cycle voltammograms of the lithium salts prepared in dimethoxyethane reveal that the reversible potentials depend upon the substituent in the para positions. In contrast the second oxidative process is only slightly affected. Comparison with similarly substituted methyl triarylmethyl anions leads to estimates of the effect of a trimethylsilyl group on carbanion, radical, and cation stability.

Original languageEnglish (US)
Pages (from-to)1243-1247
Number of pages5
JournalJournal of Organic Chemistry
Volume46
Issue number7
DOIs
StatePublished - Mar 1981
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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