Carbon–nitrogen bond cleavage in π-radicals derived by reduction of N-benzyl- and N-allyl-pyridinium salts

Abstract

Certain 1-alkyl-2,4,6-trisubstituted pyridinium salts form π-radicals by electrochemical reduction which are stable in dimethylformamide on the scale of cyclic voltammetry, whereas the corresponding 1-benzyl and 1-allyl compounds undergo carbon–nitrogen bond cleavage at measured rates which are dependent on the size of the 2,6-substituents.