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Reaction Kinetics and Catalysis Letters

, Volume 10, Issue 1, pp 77–81 | Cite as

Free-radical addition reactions initiated by metal oxides, VI

Thermally initiated and copper(II) oxide catalyzed addition of cyanoacetic acid esters to a terminal carbon-carbon double bond
  • M. Hájek
  • J. Málek
Article

Abstract

CuO catalyzed additions of ethyl cyanoacetate, initiated thermally and by di-tert-butyl peroxide, to 1-decene and ethyl 10-undecylenoate were investigated. The CuO catalyzed reaction proceeds already at 80°C at a high rate, produces 1∶1 adducts in high yields and represents the first example of catalysis in radical addition reactions of non-halogenated compounds.

Keywords

Oxide Physical Chemistry Peroxide Ethyl Catalysis 
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.

Abstract

Было исследовано присоединение зтилцианоацетата к 1-децену и зтил 10-ундециленоату, катализированное CuO, термически и ди-трет.-бутилперекисью. Реакция, катализированная CuO, протекает с высокой скоротью уже при 80°C, даваф аддукты с составом 1∶1 с высоким выходом. Эта реакция представляет собой первый пример катализа в реакциях радикального присоединеиня негалогенированных соединений.

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References

  1. 1.
    B.S. Kirkiacharian: Bull. Soc. Chim. France, 1800 (1971).Google Scholar
  2. 2.
    B.S. Kirkiacharian: Bull. Soc. Chim. France, 1797 (1971).Google Scholar
  3. 3.
    M. Hájek, J. Málek: Synthesis, 454 (1977).Google Scholar
  4. 4.
    J.C. Allen, J.I.G. Cadogan, B.W. Harris, D.H. Hey: J. Chem. Soc., 4468 (1962).Google Scholar
  5. 5.
    J.I.G. Cadogan, D.H. Hey, J.T. Sharp: J. Chem. Soc. (B), 803 (1967).Google Scholar
  6. 6.
    J.M. Surzur, P. Teissier: Bull. Soc. Chim. France, 653 (1970).Google Scholar
  7. 7.
    E.S. Huyser: Free-Radical Chain Reactions, p. 287. Wiley-Interscience, New York 1970.Google Scholar
  8. 8.
    M. Hájek, J. Málek: Synthesis, 315 (1976).Google Scholar
  9. 9.
    G.G. Smith, F.W. Kelly: Progress in Physical Organic Chemistry (Eds. A. Streitwieser, Jr. and R.W. Taft), Vol. 8, p. 75. Wiley-Intersicence, New York 1970.Google Scholar
  10. 10.
    R. Louw, E.C. Kooyman: Rec. Trav. Chim. Pays-Bas,84, 1511 (1965).Google Scholar

Copyright information

© Akadémiai Kiadó 1979

Authors and Affiliations

  • M. Hájek
    • 1
  • J. Málek
    • 1
  1. 1.Institute of Chemical Process FundamentalsCzechoslovak Academy of SciencesPrague 6Czechoslovakia

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