THE PHOTOISOMERIZATION OF 2-PHENYL-3H-INDOL-3-ONE N-OXIDE (2- PHENYLISATOGEN) TO 2-PHENYL-4H-3,1-BENZOXAZIN-4-ONE

Abstract

The use of nitrones is an important synthetic tool for the organic chemist. An unusual reaction of these nitrones is a photochemical ring expansion under proper conditions that allows the nitrone oxygen to migrate past a carbon atom in a ring and insert itself into a ring that is expanded by the oxygen. While the process occurs for a number of six-membered rings, there is only one known five member ring expansion which seems to offer a possible mechanism. This thesis discusses this mechanism and offers evidence that an isomeric oxaziridine ring created from the nitrone offers a possible explanation of the mechanism