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J Org Chem. 2008 Mar 21;73(6):2270-4. doi: 10.1021/jo702401t. Epub 2008 Feb 21.

Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles.

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1
The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

Abstract

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 degrees 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.

PMID:
18288864
DOI:
10.1021/jo702401t
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