Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reactivity and Reaction Mechanism for Reactions of 1, 1'-(Azodicarbonyl) dipiperidine with Triphenylphosphines

  • Published : 1999.08.20
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Abstract

Reactivity and reaction mechanism for the reactions of 1,1'-(azodicarbonyl) dipiperidine with triphenylphosphines are investigated using kinetic method. The cation radical, Ph3P and the anion radical, -N-N - are produced during the course of the reaction. The cation radical is formed by the transfer of an electron from phosphorus to the nitrogen atom. The anion radical is formed by the addition of the one electron to the azo rad-ical. The rate constants are decreased by electron withdrawing groups while they are increased by electron donating groups present in triphenylphosphine. The electron density increases on nitrogen, while positive charge is developed on phosphorus in the transition state.

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References

  1. Ann. Chem. Schollkopf, U.;Banhidai, B.;Frasnelli, H.;Meyer, R.;Beckhaus, H.
  2. Adv. Phys. Org. Chem. v.16 Gold, V.; Bethell, D.(Ed.)
  3. Adv. Free Radical Chem. v.2 Jenkins, A. D.
  4. J. Org. Chem. v.60 Camp, D.;Hanson, G. R.;Jenkins, I. D.
  5. J. Org. Chem. v.23 Morrison, D. C.
  6. Angew. Chem. Int. Ed. Engl. v.8 Brunn, E.;Huisgen, R.
  7. Zh. Obsch. Khim. v.30 Ginsburg, V. A.;Vasil'eva, M. N.;Dubov, S. S.;Yakubovich, A. Ya.
  8. Ph. D. Thesis, Griffth University Camp, D.
  9. J. Chem. Phys. v.23 Timmermans, J.;Martin, F.
  10. Chem. Zentr. v.Ⅰ Timmermans, J.;Martin, F.
  11. Tetrahedron Lett. Horner, L.;Schedlbauer, F.;Beck, P.
  12. J. Org. Chem. v.25 Senear, V.;Wirth, J.
  13. Philos. Mag. v.2 Guggenheim, E. A.
  14. Physical Organic Chemisty(1st ed.)(2nd ed.) Hammett, L.P.
  15. The Physical Basis of Organic Chemistry Maskill, H.
  16. Acta Chemica Scandinavia v.52 Eberson, L.;Persson, O.;Svensson, O.
  17. Macromolecules v.26 Kajiwara, A.;Konishi, V.;Morishima, V.;Schnabel, W.;Kuwata, K.;Kamachi, M.
  18. J. Chem. Soc., Perkin Trans. Yashui, S.;Fubii, M.;Kawano, C.;Nishimura, Y.;Shioji, K.;Ohno, A.
  19. J. Org. Chem. v.25 Senear, V.;Wirth, J.
  20. Aust. J. Chem. v.45 Camp, D.;Jenkins, I. D.