Silyl isoxazolines have been synthesized by [2 + 3] cycloaddition reac
tion of nitrile oxides and silylnitronates to vinyl- and allylsilanes.
The direction of the cycloaddition reaction of nitrile oxides to tria
lkoxyvinylsilanes has been shown to depend on the nature of the substi
tuents on silicon and on the method used to generate the nitrile oxide
s. The addition of silyl esters of aci-nitromethane to triethoxyvinyls
ilane gives both 5-silyl and 4-silyl isomers. The structures of silyl
isoxazolines are discussed.