By Milos Hudlicky
The current publication is basically according to the lectures at the chemistry of natural compounds of fluorine that I gave in 1969 at Virginia Polytechnic Institute in Blacksburg, Virginia, as a graduate path. References to fabric released to the tip of 1969 are integrated. The publication is basically intended to supply the historical past for one of these path, and, even as, to be a short survey of modern wisdom in, and an creation to deeper learn of, this quarter of chemistry, which has been taken care of in a few com prehensive monographs. i want to thank Professor S. C. Cohen, Syracuse collage, for the compilation of the knowledge on mass spectra and nuclear magnetic res onance spectra, and my son, Tomas Hudlicky, and my daughter, Eva Hudlickci, for his or her aid with the indexes. MILOS HUDLICKY February thirteen, 1970 Virginia Polytechnic Institute and country college Blacksburg, Virginia vii Contents bankruptcy 1. advent ......................................................... 1 improvement of Fluorine Chemistry ......................................... .
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Infrared spectroscopy is not limited to solid or liquid compounds or their solution. Since it is very sensitive, it can be applied also to gaseous compounds whose spectra can be recorded at pressures as low a few mm Hg. In addition to the infrared spectra published in current literature and in the well-known Sadtler Collection, there exist large collections of infrared spectra which can be solicited from several scientific centers, such as the Scientific Documentation Center, Dunfermline, Scotland.
CsF - 20°C, 2-3 hr (80J CFa-CF-CFa quant. (80J I OCI An extremely interesting example of addition is the reaction of perfluoroolefins with perjiuoroacyl fluorides (81) or perjiuoroaromatics [82) in the presence of cesium or potassium fluoride, respectively. Evidently, fluorine ion converts the perfluoro-olefin to a perfluoroalkyl carbanion which displaces fluoride in acyl fluorides and strongly deactivated perfluoroaromatics capable of nucleophilic displacements. The reaction is suitably designated as a "nucleophilic paraphrase of the Friedel-Crafts acylation or alkylation.
CHsONa )-0,,- 1"-=/1 AcO (C s HshCH-CHF2 47% OEt (56J (57J ADDmON OF FLUORINE TO OTHER UNSATURATED SYSTEMS Examples of the addition of fluorine across carbon-carbon triple bonds are very scarce_ The addition of fluorine to aromatic systems is usually accompanied by concomitant replacement of hydrogen by fluorine regardless of whether elemental fluorine, high-valency fluorides, or electrochemical fluorination are used (pp. 29, 30). Addition of fluorine across carbon-nitrogen bonds in nitriles, thiocy- 25 lntrocIuction of Fluorine into Organic Compounds anates, isocyanates, and isothiocyanates can be carried out using numerous reagents [58-69).