Abstract
The carbon-fluorine bond, noted for its strength1, has been of chemical interest2 even before Moissan's discovery of elemental fluorine. The most electronegative element, fluorine is uniquely capable of replacing all the hydrogen atoms in every hydrocarbon system3, yielding materials such as polytetrafluoroethylene renowned for their combination of rare physical properties, out-standing chemical inertness and high thermal stability4, with sig-nificant modern technological applications5,6. Reaction of satur-ated fluorocarbons requires extreme conditions1, for example treat-ment with metals at ∼500 °C7 or high-energy irradiation8. Following an observation by MacNicol and McGregor (unpublished data) of an unprecedented reactivity under mild conditions we now report specifically the efficient transformation of perfluorodecalin (1) to known host molecules by arenethiolate nucleophiles in dipolar aprotic solvent. This chemistry is not only of fundamental mechanistic interest, but also creates new synthetic possibilities in various fields. For example, preparing novel hosts for inclusion chemistry9, a subject attracting much current attention.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Tatlow, J. C. J. fluor. Chem. 25, 99–110 (1984).
Banks, R. E. & Tatlow, J. C. J. fluor. Chem. 35, 3–4 (1987).
Banks, R. E. & Tatlow, J. C. J. fluor. Chem. 33, 227 (1986).
Banks, R. E. Fluorocarbons and their Derivatives 16–17 (Macdonald, London, 1970).
Anderson, R. F. & Punderson, J. O. in Organofluorine Chemicals and their Industrial Applications (ed. Banks, R. E.) 235–247 (Ellis Horwood, Chichester, 1979).
Slinn, D. S. L. & Green, S. W. in Preparation, Properties, and Industrial Applications of Organofluorine Compounds (ed. Banks, R. E.) 45–82 (Ellis Horwood, Chichester, 1982).
Gething, B., Patrick, C. R., Stacey, M. & Tatlow, J. C. Nature 183, 588–589 (1959).
Florin, R. E. in Fluoropolymers (ed. Wall, L. A.) 317–380 (Wiley, New York, 1972).
Inclusion Compounds Vols 1–3 (eds Atwood, J. L, Davies, J. E. D. & MacNicol, D. D.) (Academic, London, 1984).
Barbour, R. H., Freer, A. A. & MacNicol, D. D. J. chem. Soc. chem. Commun. 362–363 (1983).
MacNicol, D. D., Mallinson, P. R. & Robertson, C. D. J. chem. Soc. chem. Commun. 1649–1651 (1985).
Smart, B. E. in Supplement D: The Chemistry of Halides, Pseudo-Halides and Azides (eds Patai, S. & Rappoport, Z.) 629–630 (Wiley, Chichester, 1983).
Wakselman, C. & Kaziz, C. J. fluor. Chem. 33, 347–358 (1986).
Liebman, J. F. J. fluor. Chem. 3, 27–33 (1974).
Miller, J. F., Hunt, H. & McBee, E. T. Analyt. Chem. 19, 148–149 (1947).
Smart, B. E., Middleton, W. J. & Farnham, W. B. J. Am. chem. Soc. 108, 4905–4907 (1986).
Wakselman, C. & Tordeux, M. J. org. Chem. 50, 4047–4051 (1985).
Liebman, J. F. J. fluor. Chem. 25, 481–486 (1984).
Hardy, A. D. U., MacNicol, D. D. & Wilson, D. R. J. chem. Soc. Perkin Trans. II 1011–1019 (1979).
Oliver, J. A., Stephens, R., Tatlow, J. C. & Taylor, J. R. J. fluor. Chem. 7, 555–568 (1976).
Maruta, M. & Ishikawa, N. J. fluor. Chem. 13, 111–122 (1979).
Le Blanc, M. & Reiss, J. G. in Preparation, Properties and Industrial Applications of Organo-fluorine Compounds (ed. Banks, R. E.) 83–138 (Ellis Horwood, Chichester, 1982).
Adcock, J. L., Inoue, S. & Lagow, R. J. J. Am. chem. Soc. 100, 1948–1950 (1978).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
MacNicol, D., Robertson, C. New and unexpected reactivity of saturated fluorocarbons. Nature 332, 59–61 (1988). https://doi.org/10.1038/332059a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/332059a0
This article is cited by
-
Treatment technologies for aqueous perfluorooctanesulfonate (PFOS) and perfluorooctanoate (PFOA)
Frontiers of Environmental Science & Engineering in China (2009)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
