Synthesis of Electron-Deficient Oxetanes. 3-Azidooxetane, 3-Nitrooxetane, and 3,3-Dinitrooxetane

Article abstract of DOI:10.1021/jo00166a003

A facile synthesis of 3-hydroxyoxetane is described and is based on the addition of acetic acid to epichlorohydrin, protection of the resulting primary alcohol as an acetal, basic acetate hydrolysis and ring closure, and removal of the protecting group. 3-Azidooxetane was prepared from 3-(tosyloxy)oxetane and sodium azide.Reduction of the azide with triphenylphosphine or hydrogen gave 3-aminooxetane, and oxidation of the amine with m-chloroperbenzoic acid gave 3-nitrooxetane.Oxidative nitration or reaction with tetranitromethane gave 3,3-dinitrooxetane. 3-Azidooxetane and 3,3-dinitrooxetane were polymerized with Lewis acids.