Chemistry:Trifluoromethyl hypofluorite
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| Names | |||
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| Preferred IUPAC name
Trifluoromethyl hypofluorite | |||
| Identifiers | |||
3D model (JSmol)
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PubChem CID
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| Properties | |||
| CF 3OF | |||
| Molar mass | 104.004012 g/mol | ||
| 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). | |||
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| Infobox references | |||
Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula CF
3OF. Its chemical structure resembles methanol, but every hydrogen atom is replaced by a fluorine atom. Trifluoromethyl hypofluorite is a toxic gas at room temperature, exploding when condensed; but in small quantities the compound is useful for certain fluorination reactions in organic chemistry.
Structure
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), the trifluoromethyl ester of hypofluorous acid.
Generation
It is prepared by the reaction of fluorine gas with carbon monoxide,[1] over a cesium fluoride catalyst:
- 2 F
2 + CO → CF
3OF
The reaction is too dangerous for commercial use. The process is highly exothermic, each reagent is either extremely toxic or corrosive, and the product is liable to explode when condensed.[2]
Reactions
The gas hydrolyzes only slowly at neutral pH.
In organic chemistry, the compound adds electrophilic fluorine to multiple bonds. It has been used for the preparation of α-fluoroketones from silyl enol ethers[3] and N-fluoroamides from iminoethers. It directly fluorinates activated arenes.[2] Behaving like a pseudohalogen, CF3OF adds to ethylene to give the ether:[citation needed]
- CF
3OF + CH
2CH
2 → CF
3OCH
2CH
2F
With saturated compounds, it usually performs an indiscriminate radical fluorination. But radical traps cause the reaction to instead selectively fluorinate tertiary carbons.[2]
References
- ↑ 1.0 1.1 Cady, G (1966). "Trifluoromethyl Hypofluorite". Inorganic Syntheses. 8. p. 168. doi:10.1002/9780470132395.ch43. ISBN 978-0-470-13167-1.
- ↑ 2.0 2.1 2.2 Hesse, Robert H. (2001). "Trifluoromethyl hypofluorite". Encyclopedia of Reagents for Organic Synthesis. Wiley. doi:10.1002/047084289X.rt251. ISBN 0-471-93623-5.
- ↑ Middleton, W. J.; Bingham, E. M. (1980). "α-Fluorination of carbonyl compounds with trifluoromethyl hypofluorite". Journal of the American Chemical Society 102 (14): 4845–6. doi:10.1021/ja00534a053. Bibcode: 1980JAChS.102.4845M.
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