Thermal Decomposition of β-Allyloxypropionyl Peroxide. Cyclization of the β-Allyloxyethyl Radical¹

Cyclic addition of hetero radicals. II. Cyclic additions of alkoxy radicals in alkenes

“…A photolysis, using the filter solution of pentenyl nitrite 3 at the concentration normally resulting in the best yield of tetrahydrofurfural oxime (10) was found to result in 10% decrease in the yield of 10. A similar photolysis at lower concentration resulted in a 4% increase in the yield of 10.…”

“…4-Pentenoxy Radical. -Irradiation of 4-pentenyl-l nitrite (3, Scheme I) yielded as the major product tetrahydrofurfural oxime (10).…”

“…noted during their study of the photolysis of n-octyl nitrite that in the presence of oxygen n-octyl nitrate was the major product and there was no nitroso dimer formation. The photolysis of pentenyl nitrite 3 in a solution that had been purged with oxygen and under an atmosphere of pure oxygen resulted in definite nitroso dimer formation and a 33% yield of tetrahydrofurfural oxime (10). Results are tabulated in Table I.…”

“…Tetrahydrofurfural Oxime (10).-The above oil recovered from the photolysis of 4-pentenyl-l-nitrite was heated for 14 hr at 45°to cleave all nitroso dimer and isomerize it to the oxime.…”