Hot Water-Promoted Ring-Opening of Epoxides and Aziridines by Water and Other Nucleopliles

Zhi Wang, Yong-Tao Cui, Zhao-Bing Xu, and Jin Qu*
The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
J. Org. Chem., 2008, 73 (6), pp 2270–2274
DOI: 10.1021/jo702401t
Publication Date (Web): February 21, 2008
Copyright © 2008 American Chemical Society

Abstract

Abstract Image

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 °C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

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History

  • Published In Issue March 21, 2008
  • Received November 10, 2007

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