Collect. Czech. Chem. Commun. 2002, 67, 1359-1365

Synthesis of (Trifluoromethyl)aziridines in 1,1,1,3,3,3-Hexafluoropropan-2-ol: First Example of Coupling Reactions of Fluoral, an Amine and a Diazo Compound

Maria Vittoria Spanedda, Benoit Crousse*, Satoru Narizuka, Danièle Bonnet-Delpon* and Jean-Pierre Bégué

BioCIS, Centre d'Etudes Pharmaceutiques, rue J. B. Clément, Châtenay-Malabry, F-92296 Cedex, France


The influence of solvent on the Yb(OTf)3 or BF3·Et2O-catalyzed reaction of (trifluoromethyl)aldimines with ethyl diazoacetate has been investigated. The reaction of fluoral ethyl hemiacetal, an aromatic amine, and ethyl diazoacetate could be performed in 1,1,1,3,3,3-hexafluoropropan-2-ol to provide the corresponding (trifluoromethyl)aziridines.

Keywords: Aziridines; Aziridination; Fluorine; Hexafluoropropan-2-ol; Imines; Diazo compounds.

References: 24 live references.