Autoxidation Reactions

  • Karl-Dietrich Gundermann
  • Frank McCapra
Part of the Reactivity and Structure: Concepts in Organic Chemistry book series (REACTIVITY, volume 23)

Abstract

The majority of these chemiluminescent reactions are weak, but notable exceptions are the oxidation of tretrakis-dimethylamino ethylene (TMAE), p. 119 and the bis-isoquinolinium salts with their reduction product (p. 120). The reaction of O2 with Grignard reagents is a long known example. Virtually any compound with C-H bonds gives detectable luminescence on oxidation, often with vanishingly low efficiency. It is thus very difficult to derive a convincing mechanism. However the study of simple model compounds has given the chain termination or Russell mechanism [1] a central place in this form of chemiluminescence. In the oxidation of polymers, where the peroxide groups are statistically far removed from each other, it is a less reasonable general mechanism. Recently evidence has been provided for hydrotrioxides as intermediates [54] produced by recombination of HO-radicals with peroxy-radicals (mostly present under the oxidation conditions). Perhaps the gas phase oxidation of methanol [2] to formaldehyde or the second radical annihilation step of the decomposition of hyponitrite esters provide better models.

Keywords

Hydrocarbon Ketone Polymethyl Methacrylate Biphenyl Vasil 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Russell, G. A., J. Amer. Chem. Soc. 79, 3871 (1957)CrossRefGoogle Scholar
  2. 2a.
    Vaidya, W. M., Proc. Roy. Soc. A 219, 572 (1964)Google Scholar
  3. b.
    Menzinger, M., Adv. Chem. Phys. 12, 1 (1980)CrossRefGoogle Scholar
  4. 3.
    Belyakov, V. A. and Vassil’ev, R. F., Photochem. Photobiol. 11, 179 (1970)CrossRefGoogle Scholar
  5. Vasil’ev, R. F. and Belyakov, V. A., Photochem. Photobiol. 6, 35 (1967) and references citedCrossRefGoogle Scholar
  6. 5.
    Vasil’ev, R. F., Progr. React. Kin. 4, 305 (1967)Google Scholar
  7. 6.
    Mendenhall, D. G., and Nathan, R. A., Angew. Chem. 89, 220 (1977); Intern. Ed. Engl. 16, 225 (1977)CrossRefGoogle Scholar
  8. 7.
    Lundeen, G. and Livingston, R., Photochem. Photobiol. 4, 1085 (1965)CrossRefGoogle Scholar
  9. 8.
    Robertson, A. and Waters, W. A., J. Chem. Soc. 1948, 1574Google Scholar
  10. 9.
    Woodward, A. E., and Mesrobian, R. B., J. Amer. Chem. Soc. 75, 6189 (1953)CrossRefGoogle Scholar
  11. 10.
    Kellogg, H. J. Amer. Chem. Soc. 91, 5433 (1969)CrossRefGoogle Scholar
  12. 11.
    Vasil’ev, R. F. and Rusina, I., Doklad. Akad. SSSR 153, 1101 (1963)Google Scholar
  13. 12.
    Vasil’ev, R. F. and Rusina, I. ibid. 153, 5433 (1963)Google Scholar
  14. 13.
    Beutel, J., J. Amer. Chem. Soc. 93, 2615 (1971)CrossRefGoogle Scholar
  15. 14.
    Howard, J. A. and Ingold, K. U., ibid. 90, 1056 (1968)Google Scholar
  16. 15.
    Nakano, M., Takayama, K. and Shimizu, Y., ibid. 98, 1974 (1976)Google Scholar
  17. 16.
    Murray, R. W., in Lit. 78), p. 59, 84Google Scholar
  18. 17.
    Krinsky, N. I., in Lit. 78) p. 597, esp. 603Google Scholar
  19. 18.
    Howard, J. A., Schwalin, W. J. and Ingold, K. U., Advan. Chemistry Series No. 75, 6 (1968)Google Scholar
  20. 19.
    Howard, J. A., Ingold, K. U. and Symonds, M., Can. Chem. J. 46, 1017 (1968)CrossRefGoogle Scholar
  21. 20.
    Middleton, B. S. and Ingold, K. U., Can. J. Chem. 45, 191 (1967)CrossRefGoogle Scholar
  22. 21.
    Lazar, M. and Matisovâ-Rychla, L., J. Luminescence 6, 167 (1973)CrossRefGoogle Scholar
  23. 22.
    Rychly, J., Matisovâ-Rychla, L. and Lazar, M., J. Polymer. Sci. Sym. 57, 139 (1976)CrossRefGoogle Scholar
  24. 23.
    Philipps, D., Anissimov, V., Karpukhin, O. and Schlyapintokh, V. Ya., Photochem. Photobiol. 9, 183 (1969)CrossRefGoogle Scholar
  25. 24.
    Vasil’ev, R. F. and Belyakov, V. A., ibid.11, 179 (1970)Google Scholar
  26. 24a.
    Forster, T., Discuss. Farad. Soc. 27, 7 (1959)CrossRefGoogle Scholar
  27. 25.
    De Kock, R. J. and P. A. H., M. Hol, Rec. Trav. chim. Pays-Bas 85, 102 (1966)CrossRefGoogle Scholar
  28. 26.
    Matisová-Rychlá, L., Lazar, M., Rychly, J. and Karpukhin, O. N., J. Polym. Sci. Sym. 40, 145 (1973)CrossRefGoogle Scholar
  29. 27.
    Richardson, W. H., Hodge, V. F., Stiggall, D. L., Yelvington, M. B. and Montgomery, F. C., J. Amer. Chem. Soc. 96, 6652 (1973)CrossRefGoogle Scholar
  30. 28.
    Bordwell, F. B. and Knight, A. C., ibid. 93, 3416 (1971)Google Scholar
  31. 29.
    Ogata, Y. and Sawaki, Y., ibid. 97, 6983 (1975)Google Scholar
  32. 30.
    Ogata, Y. and Sawaki, Y., ibid.99, 5412 (1977)Google Scholar
  33. 31.
    Kamiya, I. and Sugimoto, T., Bull. Chem. Soc. Japan 50, 2442 (1977)CrossRefGoogle Scholar
  34. 32.
    Avramoff, M. and Sprinzak, Y., J. Amer. Chem. Soc. 85, 1655 (1963)CrossRefGoogle Scholar
  35. 33.
    Ogata, Y. and Sawaki, Y., J. Org. Chem. 42, 40 (1977)CrossRefGoogle Scholar
  36. 34.
    Hiramatsu, T., Harada, T. and Yamaji, T., Bull. Chem. Soc. Japan 55, 985 (1982)CrossRefGoogle Scholar
  37. 35.
    Kamiya, I. and Sugimoto, T., ibid. 54, 25 (1981)Google Scholar
  38. 36.
    Kamiya, I. and Sugimoto, T., Chem. Lett., 335 (1978); Photochem. Photobiol. 30, 49 (1979)Google Scholar
  39. 37.
    Lofthouse, G., Suschitzky, H., Wakefield, B., Whitaker, R. and Tuck, B., J. Chem. Soc., Perkin Trans 1, 1634 (1979)CrossRefGoogle Scholar
  40. 38.
    See Gundermann, K.-D., Topics Curr. Chem. 46, 63 (1974), p. 75Google Scholar
  41. 39.
    Wedekind, F., Z. wiss. Phot. 5, 29 (1905)Google Scholar
  42. 40.
    Bardsley, R. L. and Hercules, D. M., J. Amer. Chem. Soc. 90, 4545 (1968)CrossRefGoogle Scholar
  43. 41.
    Bolton, P. H. and Kearns, D. R., ibid. 96, 4651 (1974)Google Scholar
  44. 42.
    Berlman, I. B., Handbook of Fluorescence Spectra of Aromatic Compounds Academic Press N. Y. 1971Google Scholar
  45. 43.
    Hastings, J. W. and Wilson, T., Photochem. Photobiol.23, 461 (1976)CrossRefGoogle Scholar
  46. 44.
    Shlyapintokh, V. Ya., Chemiluminescentnye Metody Issledovania Medlennych Chimiceskich Processov, p. 158, 1960Google Scholar
  47. 45.
    Thomas, J. R., J. Amer. Chem. Soc. 82, 5955 (1960)CrossRefGoogle Scholar
  48. 46.
    Matisova-Rychla, L., Karpukhin, O. N. and Pochalok, T. O., Photochem. Photobiol. 18, 303 (1973)CrossRefGoogle Scholar
  49. 47.
    Orudsheva, I. M., Suleimanova, L. G. andLiksha, V. B., Azerb. Khim. Zhurn. 1974, 51; C. A. 82, 139 x (1975)Google Scholar
  50. Matisova-Rychla, L., Ambrovic, P., Kulickova, N. and Rychly, J., J. Polym. Sci., Symposium No. 57, 181 (1976). This paper describes the influence of 2, 4, 6-trisubsti- tuted phenols (e.g. 2,6-di (t-butyl)-4-alkyl- or -cycloalkyl phenols on the autoxidation chemiluminescence of polypropyleneCrossRefGoogle Scholar
  51. 49.
    Ivanov, S. K., Yuritsin, V. S. and Shopov, D., Coll.Czech. Chem. Commun. 37, 3284 (1972); C. A. 79, 125595 k (1973)Google Scholar
  52. 50.
    Kucher, R. V., I. A. Opeida and I.N. Dumbai, Khimiya tv. topliva (Solid Fuel Chemistry) 9, (1975), Nr. 4Google Scholar
  53. 51.
    Dumbai, I. N., Kucher, V. R. and Sarancuk, V. J., ibid. 13, 67 (1979)Google Scholar
  54. 52.
    Stauff, J. and Nimmerfall, F., Z. Naturforsch. 25 b, 1009 (1969)Google Scholar
  55. 53.
    Steele, R. H. and Vorhaben, J. E., Biochemistry 6, 1404 (1967)CrossRefGoogle Scholar
  56. 54.
    Shereshovets, V. V. et al., Izv. Akad. Nauk SSR Ser. Khim. 1982, 2631Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1987

Authors and Affiliations

  • Karl-Dietrich Gundermann
    • 1
  • Frank McCapra
    • 2
  1. 1.Institut für Organische ChemieTechnische Universität ClausthalClausthal-ZellerfeldGermany
  2. 2.The School of Chemistry and Molecular SciencesThe University of SussexFalmer, BrightonUK

Personalised recommendations