Cycloaddition/ring opening of 3-unsubstituted cyclic nitronates, isoxazoline and 5,6-dihydro-4H-1,2-oxazine N-oxides, as synthetic equivalents of functionalized nitrile oxides

Article abstract of DOI:10.1016/S0040-4039(98)01903-0

ω-Halo-α-nitropropane and -butane are cyclized with a base to form cyclic nitronates as labile 1,3-dipoles. They can be trapped by a variety of monosubstituted ethenes to give 3-(2-hydroxyethyl)isoxazolines or perhydroisoxazolo[2,3-b]o-oxazines depending