Photochemistry of silylimines: Diels–Alder trapping of a photochemically generated o-quinodimethane intermediate from o-(N-trimethylsilyliminomethyl)toluene

Abstract

o-(N-Trimethylsilyliminomethyl)toluene on irradiation underwent γ-hydrogen transfer to give an o-quinodimethyane intermediate which could be trapped with dimethyl fumarate, dimethyl maleate, trans-methyl cinnamate, methyl acrylate, acrylonitrile and the imine itself; under identical conditions o-(N-t-butyliminomethyl)toluene was inert.