The reaction of (2-alkylidenaminophenyl)sulfides with di-iso-propyl peroxydicarbonate: Radical versus non-radical pathway

Article abstract of DOI:10.1016/S0040-4020(01)88475-1

The reaction of 2-methylthio- or 2-phenylthioarylimines with di-iso-propyl peroxydicarbonate (DPDC) is described. The phenylthio-derivatives undergo cyclization to benzothiazoles via a free-radical mechanism, whereas the methylthio-analogs afford arylthiomethyl iso-propyl carbonates, together with benzothiazoles as well; this last result could be accounted for with the intervention of a non-radical mechanism operating side by side with the radical one.