Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Structure and Reactivity in the Reaction of Diazoindanes and Diazoindanones with Triphenylphosphine : The Formation of Mono-, and Bisphosphazines and Hydrazone-Compounds

  • Published : 1997.09.20
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Abstract

The reactions of diazoindanes and diazoindanones with triphenylphosphine have been studied in acetonitrile. The diazoindanes and diazoindanones react with triphenylphosphazine. The reaction of 1,3-bis(diazo)indan-2-one with a tenfold excess of triphenylphosphine in dry acetonitrile gave the 1,3-bis(phosphazino)indan-2-one, however in acetonitrile containing below of 1% water, the 1,3-bis(hydrazono)indan-2-one was produced by hydrolysis. The phosphazine compound could be easily converted into bishydrazone by recrystallization, due to small amounts of water in the solvent. The reactivity of triphenylphosphine toward diazoindanes and diazoindanones depends on the structrue of the diazo compounds.

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References

  1. J. Am. Chem. Soc. v.76 Szmant, H. H.;lewitt, G.
  2. Monatsh. Chem. v.50 Pollak, J.;Gebauer-Fulnegg, E.
  3. J. Chem. Soc. v.B Ansell, G. B.
  4. J. Chem. Phys. v.29 Benson, S. W.;Buss, J. H.
  5. Chem. Rev. v.69 Benson, S. W.;Cruikshank, F. R.;Golden, D. M.;Haugen, G. R.;O'Neal, H. E.;Rodgers, A. S.;Shaw, R.;Walsh, R.
  6. Acc. Chem. Res. v.7 Moss, R. A.
  7. The Organic Chemistry of Phoshorous Kirby, A. J.;Warren, S. G.
  8. Helv. Chem. Acta v.2 Staudinger, H;Meyer, J.
  9. The Organic Chemistry of Phosphorous Kirby, A. J.;Warren, S. G.
  10. The Organic Chemist's Book of Orbitals Jorgensen, W. L.;Salem, L.
  11. J. Am. Chem. Soc. v.110 Soundarajan, N.;Platz, M. S.;jackson, J. E.;Dolyle, M. P.;Liu, H.;Anand, S. M.
  12. Can. J. Chem. v.59 Cowie, M.;Gauthier, M.-D.
  13. Bull. Korean Chem. Soc. v.15 Sung, D. D.;Shin, J. S.;Lim, G. T.;Uhm, T. S.
  14. Chem. Lett. Yamawaki, J.;Ando, T.
  15. Chem. Lett. Yamawaki, J.;Ando, T.
  16. Chem. Ber. v.97 no.5 Regitz, M.;Heck, G.
  17. Bull. Korean Chem. Soc. v.9 Lee, H. K.;Kim, H. R.;Tomioka, H.
  18. Chem. Ber. v.29 Gabriel, S.;Stelzner, R.
  19. J. Am. Chem. Soc. v.80 Cava, M. P.;Litle, R. L.;Napier, D. R.
  20. Chem. Ber. v.91 Horner, L.;Kirmse, W.;Muth, K.
  21. J. Chem. Soc.(C) Moss, R. A.;Funk, J. D.
  22. Textbook of Practical Organic Chemistry(4th ed.) Vogel, A.
  23. Reagents in Organic Chemistry(1st ed.) Fieser, L. F.;Fieser, M.
  24. J. Prakt. Chem. v.125 Curtis, T.;Kraemer, G.
  25. Dictionary of Organic Compounds v.4 Heibron, I.;Bunhury, H. M.
  26. Purification of Laboratory Chemicals(3rd ed.) Perrin, D. D.;Armarego, W. L. F.
  27. Chem. Ber. v.92 Bestmann, H. J.;Buckschewski, H.;Leube, H.
  28. The Chemistry of Diazonium and Diazo Groups Patai, S.
  29. J. Am. Chem. Soc. v.94 Borowitz, I. J.;Pames, H.;Lord, E.;Yee, K. C.
  30. Frontier Orbital and Organic Chemical Reactions Fleming, I.
  31. Adv. Phys. Org. Chem. Hine, J. part of the series, The Principle of Least Nuclear Motion v.15 Gold, V.;Bethell, D.(Ed.)