Photoinduced 1,2,3,4-tetrahydropyridine ring conversions

Abstract

Stable heterocyclic hydroperoxide can be easily prepared as a product of fast oxidation of a 1,2,3,4-tetrahydropyridine by 3O2 if the solution is exposed to sunlight. The driving force for the photoinduced electron transfer is calculated from electrochemical and spectroscopic data. The outcome of the reaction depends on the light intensity and the concentration of O2. In the solid state the heterocyclic hydroperoxide is stable; in solution it is involved in further reactions.

Keywords

• heterocyclic hydroperoxide
• oxaziridine
• photoinduced electron transfer
• pyrrolidine
• tetrahydropyridine