Formation of lactams via photoelectron-transfer catalyzed reactions of N-allylamines with α,β-unsaturated esters

Abstract

Anthraquinone photosensitized reactions of a few N-allylamines with α,β-unsaturated esters have been investigated. These reactions led predominantly to the formation of lactams along with trace amounts of products arising out of tandem radical addition reactions. A mechanism is proposed involving the rearrangement of the α-aminoallyl radical, initially generated via anthraquinone photosensitized reactions, to α-aminoalkyl radicals. Subsequent reactions of these radicals with α,β-unsaturated esters can lead to the observed products.