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Synlett 1993; 1993(11): 847-849
DOI: 10.1055/s-1993-22629
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Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene

Y. Masaki* , T. Miura, M. Ochiai
  • *Gifu Pharmaceutical University, 5-6-1 Mitahora-Higashi, Gifu 502, Japan
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Publication Date:
19 March 2002 (online)

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A π-acid, tetracyanoethylene was found to catalyze alcoholysis of epoxides at the ambient temperature to 40 °C in good yields. The stereospecific anti-opening and favorable chemoselectivity without cleavage of tetrahydropyranyl ether and ethylene acetal groups were demonstrated. In the reaction of terminal and 1,2-disubstituted epoxides, a novel regioselective opening reaction associated with anchimetric assistance of the ethereal group in the side chain was observed.

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