27. Preparation of Silicon- and Sulfur-Based Fluorinated Methane Derivatives as Versatile Fluoromethylation Reagents

  1. Herbert W. Roesky
  1. G. K. Surya Prakash and
  2. Fang Wang

Published Online: 14 OCT 2012

DOI: 10.1002/9781118409466.ch27

Efficient Preparations of Fluorine Compounds

Efficient Preparations of Fluorine Compounds

How to Cite

Prakash, G. K. S. and Wang, F. (2012) Preparation of Silicon- and Sulfur-Based Fluorinated Methane Derivatives as Versatile Fluoromethylation Reagents, in Efficient Preparations of Fluorine Compounds (ed H. W. Roesky), John Wiley & Sons, Inc., Hoboken, NJ, USA. doi: 10.1002/9781118409466.ch27

Editor Information

  1. Institut für Anorganische Chemie, Georg August Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany

Author Information

  1. Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089, USA

Publication History

  1. Published Online: 14 OCT 2012
  2. Published Print: 19 OCT 2012

ISBN Information

Print ISBN: 9781118078563

Online ISBN: 9781118409466

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Keywords:

  • silicon- and sulfur-based fluorinated, as fluoromethylation reagents;
  • CF3 moiety inertness toward nucleophiles, and synthetic challenges;
  • TMSCF3, preparation via synthetic routes;
  • reductive trifluoromethylation of TMSCl using PhSOCF3;
  • synthetic applications of PhSO2CF2H

Summary

This chapter contains sections titled:

  • Preparation of (Trifluoromethyl)Trimethylsilane (TMSCF3, The Ruppert-Prakash Reagent) as a CF3- Anion Equivalent and a Difluorocarbene Precursor

  • Preparation OF Trifluoromethyl Phenyl Sulfone (PhSO2CF3) as a CF3- Anion Equivalent

  • Preparation of Difluoromethyl Phenyl Sulfone (PhSO2CF2H) as a CF2H- Anion Equivalent and a CF22− Dianion Equivalent

  • Preparation of [(Phenylsulfonyl)Difluoromethyl] Trimethylsilane (PhSO2CF2TMS) as a CF2H Anion Equivalent

  • Preparation of Fluoromethyl Phenyl Sulfone (PhSO2CH2F) as a CH2F Anion Equivalent

  • Preparation of α-Fluorobis(Phenylsulfonyl) Methane as a CH2F Anion Equivalent

  • Preparation of S-(Difluoromethyl)-S-Phenyl-2,3,4,5- Tetramethylphenylsulfonium Tetrafluoroborate (DPTPT) as a CF2H+ Cation Equivalent

  • Preparation of S-(Fluoromethyl)-S-Phenyl-2,3,4,5- Tetramethylphenylsulfonium Tetrafluoroborate (FPTPT) as a CH2F+ Cation Equivalent

  • References