O-TOSYLGLYCOLAMIDES - CATHODIC BEHAVIOR AND REACTIVITY TOWARDS ELECTROGENERATED BASES

Cathodic reduction of O-tosylglycolamides 1 promotes two-electron clea vage of the S-O bond to give the corresponding anions. The oxygen ion evolves to glycolamides 6 and/or oxadiamides 7 depending on the nature of the substrate and the medium. In particular, if it gives rise to 6 via a self-protonation reaction with the parent molecule, the conjuga te base of the latter yields heterocycles 9 and 10 and reduced amides 11. Anionic species electrogenerated in the presence of 1 behave as a base and/or a nucleophile towards the substrate, depending on their na ture. The reduced ethylene ester 5 behaves unusually acting as a homog eneous phase electron transfer agent as well.