Regio-reversal in thermal and photochemical reduction of 10-methylacridinium ion by allylic silanes and stannanes

Abstract

Thermal reduction of 10-methylacridinium ion by allylic stannanes occurs via a polar mechanism to yield the dihydroacridines allylated at the γ-position exclusively, while the photoallylation of 10-methylacridinium ion proceeds via the photoinduced electron transfer from allylic silanes and stannanes to the singlet excited state of 10-methylacridinium ion to yield mainly the α-adducts.