79264-71-4Relevant articles and documents
Electrogeneration of Cyanomethyl Anion from Phenylsulphonylacetonitrile and Cyanomethyltrimesitylphosphonium Iodide and the Relative Acidities of XCH2CN (X=Ph3P(1+), Ph3As(1+), Mes3P(1+), or PhSO2) versus Acetic Acid in Acetonitrile
Bellamy, Anthony J.,MacKirdy, Iain S.
, p. 1093 - 1098 (2007/10/02)
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 (1-)CH2CN).Mes3P(1+)CH2CN I(1-) behaves similarly.The relative acidities of XCH2CN (X= Ph3P(1+), Ph3As(1+), Mes3P(1+), or PhSO2) versus acetic acid in acetonitrile has been studied both voltammetrically and spectrophotometrically.Ph3P(1+)CH2CN is a stronger acid than CH3CO2H; Ph3As(1+)CH2CN, Mes3P(1+)CH2CN, and PhSO2CH2CN are weaker acids than CH3CO2H.PhSO2CH2CN and Mes3P(1+)CH2CN I(1-) have been used in an electroanalytical method for studying the addition of (1-)CH2CN to various electrophiles.