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1979, 1780 ( C h e m . , 1980, 92, 6323). M . S. Ouali. M. Vaultier, and Ii. Carrie, Bull. Chim. , Purr 2, 1979, 633. 5 h), however, resulted in increased yields of the ring-opened products (222; X = H, or 0) (85%). C N D 0 / 2 calculations were reported for the ring-contraction, which is thought to proceed uia a concerted[ 1,3]-sigmatropic migration of the nitrogen to a carbon of the enolate anion that is formed when a bond ruptures. r. spectra indicated that compounds (224) exist predominantly as the trans-conformers.

Ichikawa, Bull. Chem. , 1979, 52, 1743. Three-Membered Ring Systems 19 attack on the carbon atom of the conjugate acid, leading to inversion, o r ( b )via an intermediate that is of carbo-cation nature, giving retention. The latter mechanism becomes more important as the reaction temperature is raised. 66 The (phenoxymethy1)oxirans thus formed may be converted into threoand erythro-1-aryloxy-3-(alkylamino)butan-2-ols by heating under reflux with aqueous solutions of alkyl-amines. "~ 'I7 'I9 H. Tucker, J.

A k a d . Nauk SSSR, Ser. , 1979, 1257 (Chem. , 1979,91, 123 306). M. A. Mohammadai and W. V. F. Brooks, J. Mol. , 1979, 7 8 , 89. C. Fridh, J. Chern. ,Faraday Trans. 2, 1979, 7 5 , 993. Three-Membered Ring Systems (88) 15 (89) (90) The reaction of oxiran with H F to yield C H 2 F C H 2 0 Hwas chosen as the model for the ring-opening of epoxides that is caused by halogen acids, and theoretical ab initio calculations for the reaction were p e r f ~ r m e d . ' ~For the gas-phase reaction, the preferred mechanism leads to retention of configuration at the carbon atoms of the ring.

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