Advertisement

Anodic functionalization of olefins in alcohols in the presence of halide salts

  • M. N. Élinson
  • I. V. Makhova
  • G. I. Nikishin
Organic Chemistry
  • 56 Downloads

Abstract

Electrolysis of conjugated, unbranched arylolefins in the presence of alkali metal halides in alcohols affords 1-aryl-2-bromoketals in 60–90% yields. Under these conditions, 2-methyl-1-phenylprop-1-ene is converted into 1-bromo-2-methyl-1-phenylprop-1-ene in 80% yield, and arylolefins with no benzylidene hydrogens give 1-aryl-1-alkoxy-2-bromoalkanes.

Keywords

Hydrogen Alcohol Alkali Metal Halide Metal Halide 
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.

Literature cited

  1. 1.
    Y. Ueno, M. Bahry, and M. Okawara, Tetrahedron Lett., 4607 (1977).Google Scholar
  2. 2.
    USSR Inventor's Certificate No. 1,331,425; Byull. Izobret., No. 30, 262 (1987).Google Scholar
  3. 3.
    E. S. Kende, Organic Reactions [Russian translation], IL, Moscow (1965), Coll. 11, p. 267.Google Scholar
  4. 4.
    J. P. Rieu, A. Boucherie, H. Gousse, et al., Tetrahedron,42, 4095 (1986).Google Scholar
  5. 5.
    T. Kageyama, Y. Tobito, A. Katoh, et al., Chem. Lett., 1481 (1983).Google Scholar
  6. 6.
    W. F. Berkowitz, I. Sasson, P. S. Sarapathkumar, et al., Tetrahedron Lett., 1641 (1979).Google Scholar
  7. 7.
    S. I. Zav'yalov and I. V. Sitkareva, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2408 (1985).Google Scholar
  8. 8.
    M. N. Élinson, I. V. Makhova, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1829 (1988).Google Scholar
  9. 9.
    G. I. Nikishin, M. N. Élinson, and I. V. Makhova, Tetrahedron Lett., 1603 (1988).Google Scholar
  10. 10.
    M. N. Élinson, I. V. Makhova, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1569 (1987).Google Scholar
  11. 11.
    V. M. Gittins, E. Wyn-Jones, and R. F. White, Internal Rotation of Molecules [Russian translation], Mir, Moscow (1977), p. 352.Google Scholar
  12. 12.
    W. Kitching, H. A. Olszowy, and K. Harvey, J. Org. Chem., 1983 (1982).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • M. N. Élinson
    • 1
  • I. V. Makhova
    • 1
  • G. I. Nikishin
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations