Photochemical reactivity of aldimines from 2,2-dimethyl-3-oxo-3-phenylpropanal

Abstract

The syntheses of some thermally labile aldimines of 2,2-dimethyl-3-oxo-3-phenylpropanal are described. The aldimines (7a–c) are photochemically reactive and undergo fission mainly into isopropyl phenyl ketone. Several other minor products are also formed. One aldimine, from aniline, (7d) is photochemically inert. The mechanism of the reaction is discussed in terms of fission of the α, β-bond perhaps involving an electron transfer process.