Journal of Organic Chemistry 2002-07-26

A new bis(2,2,2-trifluoroethyl)phosphonate for the synthesis of Z-unsaturated N-methoxy-N-methylamides.

Samuel Fortin, Félix Dupont, Pierre Deslongchamps

Index: J. Org. Chem. 67(15) , 5437-9, (2002)

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Abstract

The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.