Photochemical Reactions of N,N'-Dimethylimidazolidinetrione with Alkenes. Solvent-Incorporated Addition via Hydrogen Abstraction

Article abstract of DOI:10.1021/jo00271a022

Photoreactions of N,N'-dimethylimidazolidinetrione (1) with alkenes in benzene gave oxetanes in high yields.The reaction of 1 with stilbene proceeded via excitation of the alkene rather than 1, whereas that with 2,5-dimethylhexadiene took place via excitation of the ground-state complex of 1 with the diene.On irradiation in hydrogen-donating solvents such as alcohols, toluene, or cyclohexane, 1 underwent a quite rare solvent-incorporated addition to the alkenes via intermolecular hydrogen abstraction.