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

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, Email: qujinnankai.edu.cn

Z. Whang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem., 2008, 73, 2270-2274.

DOI: 10.1021/jo702401t (free Supporting Information)


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Abstract

Effective hydrolysis of epoxides and aziridines was conducted in water at 60 or 100C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. Hot water acts as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

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Key Words

1,2-diols, 1,2-amino alcohols


ID: J42-Y2008-0710