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Benzotrifluoride and Derivatives: Useful Solvents for Organic Synthesis and Fluorous Synthesis

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Modern Solvents in Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 206))

Abstract

Benzotrifluoride (BTF, trifluoromethylbenzene, α,α,α-trifluorotoluene, C6H5CF3) and related compounds are introduced as new solvents for traditional organic synthesis and for fluorous synthesis. BTF is more environmentally friendly than many other organic solvents and is available in large quantities. BTF is relatively inert and is suitable for use as a solvent for a wide range of chemistry including ionic, transition-metal catalyzed and thermal reactions. It is especially useful for radical reactions, where it may replace benzene as the current solvent of choice for many common transformations. BTF and related solvents are also crucial components of fluorous synthesis since they can dissolve both standard organic molecules and highly fluorinated molecules. This chapter provides an overview of the reactivity and toxicological properties of BTF and analogs and then summarizes their recent uses as reaction solvents in both traditional organic and new fluorous synthesis.

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Author information

Authors and Affiliations

  1. Occidental Chemical Corporation, Technology Center, Grand Island, NY, 14072, USA

    James J. Maul

  2. Occidental Chemical Corporation, Niagara Falls, NY, 14303, USA

    Philip J. Ostrowski

  3. Occidental Chemical Corporation, Dallas, TX, 75244, USA

    Gregg A. Ublacker

  4. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA, 15260, USA

    Bruno Linclau & Dennis P. Curran

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  1. James J. Maul
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  2. Philip J. Ostrowski
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  3. Gregg A. Ublacker
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  4. Bruno Linclau
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  5. Dennis P. Curran
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Editors and Affiliations

  1. Institut für Organische Chemie, Ludwig Maximilians-Universität München, Butenanderstr. 5 - 13, D-81377, München, Germany

    Paul Knochel

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© 1999 Springer-Verlag Berlin Heidelberg

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Maul, J.J., Ostrowski, P.J., Ublacker, G.A., Linclau, B., Curran, D.P. (1999). Benzotrifluoride and Derivatives: Useful Solvents for Organic Synthesis and Fluorous Synthesis. In: Knochel, P. (eds) Modern Solvents in Organic Synthesis. Topics in Current Chemistry, vol 206. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48664-X_4

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  • DOI: https://doi.org/10.1007/3-540-48664-X_4

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  • Print ISBN: 978-3-540-66213-6

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