Advertisement

Synthesis, Chemistry, and Anodic Oxidation of 1,2-Bis(Trialkylsilyl)Ethanes

  • Albert J. Fry
  • John M. Porter
  • Xiangyang Xuan
  • Burchelle Blackman
  • Brian Mayers
  • Daniel Hsu
  • Shayna White
Conference paper

Abstract

1,2-Bis[trialkyl-l,2-diarylethanes can be prepared by cathodic dimerization of alpha-trialkylsilyl benzyl bromides and metal-induced (Mg, HMPA; Li, THF) bis-silylation of substituted stilbenes. These substances are synthetic equivalents of both vicinal cations (by anodic oxidation in the presence of nucleophiles) and vicinal dianions (by fluoride-induced cleavage in the presence of electrophiles). A variety of experiments exploring the scope and limitations of this principle are described.

Keywords

Anodic Oxidation Alkyl Halide Benzyl Bromide Silyl Group Benzyl Cation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. (1).
    A. J. Fry, J. M. Porter, and P. F. Fry, J. Org. Chem., 1996, 61, 3191.CrossRefGoogle Scholar
  2. (2).
    A. S. Pilcher, H. L. Ammon, and P. DeShong, J. Am. Chem. Soc., 1995, 117, 5166.CrossRefGoogle Scholar
  3. (3).
    A. S. Pilcher and P. DeShong, J. Org. Chem., 1996, 61, 6901.CrossRefGoogle Scholar
  4. (4).
    T. Koizumi, T. Fuchigami, and T. Nonaka, Electrochim. Acta, 1988, 33, 1635.CrossRefGoogle Scholar
  5. (5).
    J.-i. Yoshida, T. Murata, and S. Isoe, Tetrahedron Leu., 1986, 27, 3373.CrossRefGoogle Scholar
  6. (6).
    J. Dunogues, R. Calas, N. Duffaut, P. Lapouyade, and J. Gerval, J. Organomet. Chem. 1969, 20, P20.CrossRefGoogle Scholar
  7. (7).
    D. R. Weyenberg, L. H. Toporcer, and A. E. Bey, J. Org. Chem., 1965, 30, 4096.CrossRefGoogle Scholar

Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Albert J. Fry
    • 1
  • John M. Porter
    • 1
  • Xiangyang Xuan
    • 1
  • Burchelle Blackman
    • 1
  • Brian Mayers
    • 1
  • Daniel Hsu
    • 1
  • Shayna White
    • 1
  1. 1.Chemistry DepartmentWesleyan UniversityMiddletownUSA

Personalised recommendations