“Fluorocarbons” -Alex J. Roche A Graduate Level Advanced Organic Course Rutgers, The State University of New Jersey 56:160:519 Office: Sci 311 Labs: Sci 309, 328F, 304A
[email protected] Tel: (856) 225-6166 Fax: (856) 225-6506 http://crab.rutgers.edu/~alroche/ “Fluorine leaves nobody indifferent; it inflames emotions be that affections or aversions. As a substituent, it is rarely boring, always good for a surprise, but often completely unpredictable” – Manfred Schlosser, 1998. 1 Fluorocarbons Fluorocarbons are organic compounds that contain fluorine, and they are (almost always) synthetic or man made compounds. Compounds bearing a C-F bond do not occur in nature (almost true). Thus the replacement of a C-H bond with a C-F bond gives rise to a potentially vast man made organic chemistry. Adds an entirely synthetic extra dimension to Organic Chemistry. Fluorocarbons can Provide: New Chemistry Unique Chemistry (Special Effects) New materials New Applications 2 Organofluorine Chemists (should) Aim to: -Develop the Organic Chemistry of compounds that contain Fluorine -Encourage application by collaboration with industry -Integrate the subject on a mechanistic basis with modern organic chemistry (get to a level of understanding so F is predictably unique) 3 History Hydrogen Fluoride was first reported by Scheele in 1771. The first reported synthesis of an organofluorine compound was in 1836, when Dumas and Peligot reported the synthesis of fluoromethane. It was in 1886 that Henri Moissan prepared and isolated molecular elemental fluorine gas (F2). Moissan in 1890 erroneously reported the isolation of carbon tetrafluoride as a product of the reaction of fluorine and carbon.