M. Kol, S. Rozen, E. Appelman
Mar 1, 1991
Citations
0
Influential Citations
35
Citations
Journal
Journal of the American Chemical Society
Abstract
Methyl hypofluorite (CH 3 OF) has been prepared by the reaction of elemental fluorine with methanol in acetonitrile or propionitrile at low temperature. It was removed from the reaction mixture in a stream of nitrogen and purified by fractional distillation. The compound is moderately long-lived, although the liquid has exploded upon rapid warming. The liquid compound has a freezing point of about −142°C, and vapor pressure measurements indicate a normal boiling point of −32.6±0.9°C and an enthalpy of vaporization of 23.37±0.26 kJ/mol. The infrared spectrum of the vapor is consistent with the molecule being isostructural with CH 3 OH and CF 3 OF. The compound has also been characterized by mass spectrometry and by 1 H, 19 F, and 13 C NMR spectrometries. This novel reagent adds across various double bonds to form the corresponding fluoro methoxy adducts, which are not easily accessible by other methods