Abstract
Contrary to a previous report, PhSO2CH2CN has been shown to exhibit a one-electron reduction (two-electron reductive cleavage followed by deprotonation of PhSO2CH2CN by –CH2CN). Mes3PH2CN I– behaves similarly. The relative acidities of XCH2CN (X = Ph3P+, Ph3As+, Mes3P+, or PhSO2)versus acetic acid in acetonitrile has been studied both voltammetrically and spectrophotometrically. Ph3PH2CN is a stronger acid than CH3CO2H; Ph3AsCH2CN, Mes3PH2CN, and PhSO2CH2CN are weaker acids than CH3CO2H. PhSO2CH2CN and Mes3-PCH2CN I– have been used in an electroanalytical method for studying the addition of –CH2CN to various electrophiles.
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