Reactions of 2-oxo-2-polyfluoroalkyl-sulfones and –sulfamides with nucleophiles

GRAPHICAL ABSTRACT

Abstract

Reactions of 2-oxo-2-polyfluoroalkyl-sulfones and -sulfamides with heteronucleophiles—amines, alcohols, thiols and trialkyl phosphites—are studied. 2-Oxo-2-polyfluoroalkyl-sulfones and -sulfamides react with primary arylamines affording 2-imino-2-polyfluoroalkyl-sulfones and -sulfamides, whereas reactions with primary alkylamines and secondary amines result in the formation of alkylammonium enolate salts. Treatment of 2-oxo-2-polyfluoroalkyl-sulfones and -sulfamides with alcohols and thiols gives hemi(thio)ketals. Reactions of 2-oxo-2-trifluoromethyl-sulfones(-sulfamides) with trimethyl phosphite produce equimolar mixture of dimethyl(3-sulfonyl-1,1,1-trifluoropropan-2-yl)phosphate and 3,3,3-trifluoro-2-methoxy-1-sulfonylprop-1-ene.

KEYWORDS:

• β-Ketosulfone
• β-ketosulfamide
• polyfluoroalkyl
• nucleophilic addition
• imine
• trialkyl phosphite

Acknowledgments

The authors thank Dr. Vladimir V. Trachevsky, the Joint Use Center of NMR Spectroscopy at the G.V. Kurdyumov Institute for Metal Physics of NAS of Ukraine, Kyiv, Ukraine, for recording the NMR spectra.