Benzaldehyde Oxime as a 1,3-Dipole Chameleon

Article abstract of DOI:10.1021/jo00226a050

Reaction of the iminium salt derived from benzaldehyde oxime and (trimethylsilyl)methyl triflate with cesium fluoride in the presence of electron-dificient alkenes gives rise to azomethine ylide cycloadducts.In sharp contrast, reaction of the salt with alkynes produces dipolar cycloadducts derived from nitrones.