Intramolecular orientation at the micellar interface: control of norrish type I and type II reactivity of benzoinalkylethers via conformational effects

Abstract

The photolysis of benzoinalkylethers 1-5 solubilized in detergents show a significant deviation from the course of reaction in isotropic organic solvents. Remarkable difference in photobehaviour is noticed between the short chain (1-3) and the long chain (4 and 5) benzoinalkylethers in the micellar media. However, the influence of the micellar media on the photobehaviour of alkyldeoxybenzoins 6 and 7 was small. The importance of 'cage effect' in controlling the product distribution was evident from its dependence on the micellar size and on the occupancy number. More importantly, a comparative analysis of the photobehaviour of the ketone 1-7 reveals that the micellar interface can be used to control the conformations of organic molecules.