Electron-transfer-induced photochemical reactions of (silylallyl)iminium and benzylpyrrolinium salts by dual diradical and diradical cation cyclization pathways

Abstract

The electron-transfer-induced photocyclization reactions of a series of N- and C-silylmethallyl-substituted iminium and 1-benzyl-1-pyrrolinium salts have been investigated in order to gain information about their mechanistic course and to probe their synthetic potential. The results obtained from these studies demonstrate that diradical cation intermediates formed in these processes can be transformed to products via two competing mechanistic pathways involving radical coupling or loss of allylic or benzylic electrofugal groups