Conversion of alcohols into amides by chlorodiphenylmethylium hexachloroantimonate in nitrile solvents; some further reactions of the triphenylmethyl cation

Abstract

Treatment of alcohols with the cations chlorodiphenylmethylium (I), dichloro(phenyl)methylium (II), and pentachloroallylium (III) in nitrile solvents gives the nitrilium ions derived from the alcohols, which on quenching with water give the corresponding amides. Quenching the nitrilium ions with suitable nucleophiles provides tetrazoles, thioamides, amidines, and amidates. Certain limitations on the oxidations by triphenylmethyl cation reported previously are described.