Intramolecular electron transfer in the novel photoreaction of some β,γ-unsaturated oxime–boron trifluoride complexes. A new synthetic path to dihydroisoxazoles
Abstract
β, γ-Unsaturated oximes are photochemically reactive in benzene solution when irradiated in the presence of boron trifluoride–diethyl ether; typically 2,2-dimethyl-4,4-diphenylbut-3-enal oxime affords a low yield of 2,2-diphenyl-3,3-dimethylcyclopropanecarboxaldehyde by the aza-di-π-methane rearrangement, and a principal product (48%) identified by X-ray diffraction analysis as 4, 4-dimethyl-5-(diphenylhydroxymethyl)-4,5-dihydroisoxazole.