Thermal and photochemical reactivity of β,γ-unsaturated oximes in the presence of SnCl4

2002 ARKIVOC  
The thermal reaction of some symmetrically substituted β,γ-unsaturated oximes 2a-d in the presence of one equivalent of tin tetrachloride in toluene leads to the formation of 5,6-dihydro-4H-1,2-oxazines 3a-d. The photochemical reaction follows a different path and yields 5-(diarylhydroxymethyl)-4,4-dimethyl-4,5-dihydroisoxazoles 6a, b. A cationic mechanism is proposed for the thermal cyclisation while the photochemical process is thought to involve an SET process.
doi:10.3998/ark.5550190.0003.314 fatcat:g6k2nvbqyrdw7nn2qtjwcdxlim