Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite
Identifiers
373-91-1 N
ChemSpider 71322
Jmol interactive 3D Image
PubChem 78989
Properties
OCF
4
Molar mass 104.004012
Appearance Colourless gas
Melting point −213 °C (−351.4 °F; 60.1 K)
Boiling point −95 °C (−139 °F; 178 K)
Hazards
Main hazards Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YesYN ?)
Infobox references

Trifluoromethyl hypofluorite is an organofluorine compound with the formula CF
3
OF
. It exists as a colorless gas at room temperature and is highly toxic.[1] It is a rare example of a hypofluorite (compound with an O-F bond). It is prepared by the fluorination of carbon monoxide:

2 F2 + CO → CF3OF

The gas hydrolyzes only slowly at neutral pH.

Use in organic chemistry

The compound is a source of electrophilic fluorine. It has been used for the preparation of α-fluoroketones from silyl enol ethers.[2] Behaving like a pseudohalogen, it adds to ethylene to give the ether:

CF3OF + CH2CH2 → CF3OCH2CH2F

References

  1. Cady, G (1966). "Trifluoromethyl Hypofluorite". Inorganic Syntheses 8: 168. doi:10.1002/9780470132395.ch43.
  2. Middleton, W. J.; Bingham, E. M. (1980). "α-Fluorination of carbonyl compounds with trifluoromethyl hypo fluorite". Journal of the American Chemical Society 102: 4845–6. doi:10.1021/ja00534a053.


This article is issued from Wikipedia - version of the Monday, November 02, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.