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Synthesis 1990; 1990(2): 106-109
DOI: 10.1055/s-1990-26800
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The Synthesis of Oxiranes and Oxetanes from 1,2- or 1,3-Halohydrins Using Organoantimony(V) Alkoxide

Masahiro Fujiwara* , Kazuhisa Hitomi, Akio Baba, Haruo Matsuda
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565, Japan
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Publication Date:
17 September 2002 (online)

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Tetraphenylstibonium methoxide (1) is an effective reagent for the synthesis of oxiranes and oxetanes from the corresponding 1,2- and 1,3-halohydrins, respectively. As the reaction conditions are neutral, oxiranes bearing an ester moiety were obtained intact without undergoing solvolysis. In addition, oxetanes, whose preparation was not generally facile, were formed in good yields under mild conditions (60-80°C).