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Triethylamine tris(hydrogen fluoride) (b. p. 5 mbar) does not etch glass and can be handled in ordinary glassware even at elevated temperatures. A more recent development, more acidic variants of “tamed HF”, are HF–dialkyl ether complexes such as Me2O p 2HF [60]. As a result of these developments, in preparative fluoroorganic chemistry there usually is no longer any need to use anhydrous hydrofluoric acid. This most hazardous reagent can usually be replaced by some kind of “tamed HF” with customtailored acidity and nucleophilicity.

Peters, Adv. Enzymol. Rel. Subj. Biochem. 1957, 113–159. 37 C. Hogue, Chem. Eng. News 2003 (April 21), 9. 38 R. Fields, Nuclear Magnetic Resonance, in: Fluorine: The First Hundred Years (1886-1986), R. E. Banks, D. W. A. Sharp, J. C. , Elsevier Sequoia, Lausanne, Switzerland, 1986, p. 287, and references cited therein. 39 St. Berger, S. -O. Kalinowski, 19F-NMR-Spektroskopie, in: NMR-Spektroskopie von Nichtmetallen, Vol. 4, Georg Thieme, Stuttgart–New York, 1994. 1 Perfluorination and Selective Direct Fluorination Shortly after their first isolation of elemental fluorine in 1886, Moissan and his coworkers treated several organic substrates with this highly reactive gas.

W. Heisey, R. P. Wayne, P. Biggs, C. E. Canosa-Mas, H. W. Sidebottom, J. Treacy, Geophys. Res. Lett. 1994, 21, 101. 29 A. McCulloch, J. Fluorine Chem. 2003, 123, 21–29. 30 A. McCulloch, J. Fluorine Chem. 1999, 100, 163–173. 31 W. T. Sturges, T. J. Wallington, M. D. Hurley, K. P. Shine, K. Shira, A. Engel, D. E. Oram, S. A. Penkett, R. Mulvaney, C. A. M. Brenninkmeijer, Science 2000, 289, 611–613. 32 (a) U. S. Environmental Protection Agency. html; (b) M. F. Gerstell, J. S. Francisco, Y. L. Yung, C.

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