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Synthesis, characterization, and reaction chemistry of tert-butyl hypofluorite
- Source :
- Journal of the American Chemical Society. 115:1379-1382
- Publication Year :
- 1993
- Publisher :
- American Chemical Society (ACS), 1993.
-
Abstract
- tert-Butyl hypofluorite ((CH[sub 3])[sub 3]COF) can be synthesized by the low-temperature reaction of elemental fluorine with tert-butyl alcohol dissolved in propionitrile or acetonitrile. The isolated compound, which melts around -94[degrees]C and has an extrapolated boiling point of about +40[degrees]C, has been characterized by mass, NMR, and IR spectrometry. The [sup 19]F NMR shift of +67 ppm lies between the corresponding shifts of HOF and CH[sub 3]OF and implies a rather high O-F bond energy. Although sterically crowded, tert-butyl hypofluorite adds to olefins to form [beta]-fluoro-tert-butoxy compounds. Addition is mainly in an anti mode, and the regioselectivity corresponds to the action of a hitherto unknown tert-butoxylium electrophile. Also formed are adducts containing F and CH[sub 2]CN, the latter deriving from the acetonitrile solvent. 19 refs., 1 tab.
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 115
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi...........ab1c593c549e3f46b742a163e9bb3cfa