2-Oxomorpholin-3-YL Radicals

  • Tad H. Koch
Chapter
Part of the NATO ASI Series book series (ASIC, volume 189)

Abstract

2-Oxomorpholin-3-yl radicals are formed when their dimers bi(2-oxomorpholin-3-yl) are dissolved. The dimer radical equilibrium constant for 3, 5, 5-trimethyl-2-oxomorpholin-3-yl varies between 1×10−9 and 6×10−16 as a function of medium, consistent with a dipolar radical structure. Variously substituted oxomorpholinyls and diiyls have been synthesized and studied. They are mild one electron reducing agents and are useful for in vitro and in vivo reduction of anthracycline anti-tumor drugs.

Keywords

Macro Cycle Ethyl Pyruvate Hyperfine Coupling Constant Silver Cation Quinone Methide 
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.
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References

  1. 1.
    Koch, T.H.; Olesen, J.A.; DeNiro, J. J. Am. Chem. Soc. 1975, 97, 7285.CrossRefGoogle Scholar
  2. 2.
    Viehe, H.G.; Merenyi, R.; Janousek, Z. Angew. Chem. Int. Ed. Engl. 1979, 18, 917.CrossRefGoogle Scholar
  3. 3.
    Baldock, R.W.; Hudson, P.; Katritzky, A.R.; Soti, F. J. Chem. Soc., Perkin Trans. 1 1974, 1422.Google Scholar
  4. 4.
    Balaban, A.T.; Caprois, M.T.; Negoita, N.; Bàican, R. Tetrahedron 1977, 33, 2249.CrossRefGoogle Scholar
  5. 5.
    Leroy, G. Adv. Quant. Chem. 1985, 17, 1.CrossRefGoogle Scholar
  6. 6.
    Koch, T.H.; Olesen, J.O.; DeNiro, J. J. Org. Chem. 1975, 40, 14; Barone, A.D.; Ph.D. Thesis, University of Colorado 1982.CrossRefGoogle Scholar
  7. 7.
    Bennett, R.W.; Wharry, D.L.; Koch, T.H. J. Am. Chem. Soc. 1980, 102, 2345.CrossRefGoogle Scholar
  8. 8.
    Himmelsbach, R.J.; Barone, A.D.; Koch, T.H. J. Org. Chem. 1983, 48, 2989; Kleyer, D.L.; Haltiwanger, R.C.; Koch, T.H. ibid, 147.CrossRefGoogle Scholar
  9. 9.
    Olson, J.B.; Koch, T.H.; J. Am. Chem. Soc. 1986, 108, in press.Google Scholar
  10. 10.
    Burns, J.M.; Wharry, D.L.; Koch, T.H. J. Am. Chem. Soc. 1981, 103, 948.CrossRefGoogle Scholar
  11. 11.
    Haltiwanger, R.C.; Koch, T.H.; Olesen, J.A.; Kim, C.S.; Kim, N.K. J. Am. Chem. Soc. 1977, 99, 6327.CrossRefGoogle Scholar
  12. 12.
    Houk, K.N.; Rondan, N.G.; Mareda, J. J. Am. Chem. Soc. 1984, 106, 4291; Houk, K.N.; Rondan, N.G. ibid., 4291.CrossRefGoogle Scholar
  13. 13.
    Gaudiano, G.; Sweeney, K.; Haltiwanger, R.C.; Koch, T.H. J. Am. Chem. Soc. 1984, 106, 7628.CrossRefGoogle Scholar
  14. 14.
    Barone, A.D.; Atkinson, R.F.; Wharry, D.L.; Koch, T.H. J. Am. Chem. Soc. 1981, 103, 1606.CrossRefGoogle Scholar
  15. 15.
    Kleyer, D.L.; Koch, T.H. J. Am. Chem. Soc. 1984, 106, 2380.CrossRefGoogle Scholar
  16. 16.
    Averbuch, S.D.; Gaudiano, G.; Koch, T.H.; Bachur, N.R. Cancer Res., 1985, 45, 6200.Google Scholar
  17. 17.
    Averbuch, S.D.; Gaudiano, G.; Koch, T.H.; Bachur, N.R. J. Clin. Oncol. 1986, 4, 88.Google Scholar

Copyright information

© D. Reidel Publishing Co. 1986

Authors and Affiliations

  • Tad H. Koch
    • 1
  1. 1.Department of Chemistry and BiochemistryUniversity of ColoradoBoulderUSA

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