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Synthesis of electron-deficient oxetanes. 3-Azidooxetane, 3-nitrooxetane, and 3, 3-dinitrooxetane

K Baum, PT Berkowitz, V Grakauskas…

文献索引:Baum, Kurt; Berkowitz, Phillip T.; Grakauskas, Vytautas; Archibald, Thomas G. Journal of Organic Chemistry, 1983 , vol. 48, # 18 p. 2953 - 2956

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被引用次数: 28

摘要

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-(tosy1oxy) oxetane and sodium azide. Reduction of the azide with triphenylphosphine or hydrogen gave 3-aminooxetane, and oxidation of the amine with m- ...