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Photochemical reactivity of keto imino ethers

Type I. Rearrangement and (2+2)-photocycloaddition to the carbon-nitrogen double bond

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Organic Chemistry and Theory

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References

  1. Chapman, O. L., Lenz, G.: Org. Photochem. 1, 283 (1967); Eaton, P. E.: Acc. Chem. Res. 1, 50 (1968); De Mayo, P.: Acc. Chem. Res., 4, 41 (1971); Bauslaugh, P. G.: Synthesis 2, 287 (1970)

    Google Scholar 

  2. Arnold, D. R.: Adv. Photochem. 6, 301 (1968); Turro, N. J., Dalton, J. C., Dawes, K., Farrington, G., Hautala, R., Morton, D., Niemczyk, M., Schore, N.: Acc. Chem. Res. 5, 92 (1972)

    CAS  Google Scholar 

  3. Corey, E. J., Nozoe, S.: J. Am. Chem. Soc. 86, 1652 (1964); Dilling, W. L.: Photochem. and Photobiol. 25, 605 (1977)

    CAS  Google Scholar 

  4. Searles, S. Jr., Clasen, R. A.: Tetrahedron Lett. 1965, 1627

    Google Scholar 

  5. Ohta, H., Tokumaru, K.: Bull. Chem. Soc. Japan 48, 1669 (1975)

    CAS  Google Scholar 

  6. Kan, R. O., Furey, R. L.: J. Am. Chem. Soc. 90, 1666 (1968)

    Article  CAS  Google Scholar 

  7. Padwa, A., Bergmark, W., Pashayan, D.: J. Am. Chem. Soc. 90, 4458 (1968); 91, 2653 (1969)

    CAS  Google Scholar 

  8. Tsuge, O., Tashiro, M., Oe, K.: Tetrahedron Lett. 1968, 3971

    Google Scholar 

  9. Oe, K., Tashiro, M., Tsuge, O.: J. Org. Chem. 42, 1496 (1977)

    Article  CAS  Google Scholar 

  10. Eaton, P. E.: J. Am. Chem. Soc. 84, 2454 (1962)

    CAS  Google Scholar 

  11. Corey, E. J., Bass, J. D., LeMahieu, R., Mitra, R. B.: J. Am. Chem. Soc. 86, 5570 (1964)

    CAS  Google Scholar 

  12. de Mayo, P., Pete, J.-P., Tchir, M.: Can. J. Chem. 46, 2535 (1968)

    Google Scholar 

  13. Padwa, A., Albrecht, F.: J. Am. Chem. Soc. 96, 4849 (1974)

    CAS  Google Scholar 

  14. Koch, T. H., Sluski, R. J.: Tetrahedron Lett. 1970, 2391

    Google Scholar 

  15. Comstock, W. J., Wheeler, H. L.: Am. Chem. J. 13, 522 (1891)

    Google Scholar 

  16. Crockett, G. C., Koch, T. H.: J. Org. Chem. 42, 2721 (1977)

    Article  CAS  Google Scholar 

  17. Crockett, G. C., Koch, T. H.: J. Org. Chem. 42, 2721

    Google Scholar 

  18. Koch, T. H., Sluski, R. J., Moseley, R. H.: J. Am. Chem. Soc. 95, 3957 (1973)

    CAS  Google Scholar 

  19. Sluski, R. J.: Masters Thesis, University of Colorado 1971

    Google Scholar 

  20. Burns, J. M., Ashley, M. E., Crockett, G. C., Koch, T. H.: J. Am. Chem. Soc. 99, 6924 (1977)

    Article  CAS  Google Scholar 

  21. Haltiwanger, R. C., Burns, J. M., Crockett, G. C., Koch, T. H.: J. Am. Chem. Soc., submitted (1977)

    Google Scholar 

  22. Al-Jallo, H. N. A., Waight, E. S.: J. Chem. Soc. B 1966, 73

    Google Scholar 

  23. Herz, W., Iyer, V. S., Nair, M. G., Saltiel, J.: J. Am. Chem. Soc. 99, 2704 (1977)

    Article  CAS  Google Scholar 

  24. The computer program used for these calculations is a modified version of the original program as described by R. Hoffmann: J. Chem. Phys. 39, 1397 (1963). For a description of the modified program see S. S. Zumdahl: Ph. D. Thesis, University of Illinois 1968

    Article  CAS  Google Scholar 

  25. Lamola, A. A., Hammond, G. S.: J. Chem. Phys. 43, 2129 (1965)

    Article  CAS  Google Scholar 

  26. Woodward, R. B., Hoffmann, R.: Angew. Chem., Int. Ed. Engl. 8, 781 (1969)

    Article  CAS  Google Scholar 

  27. Dewar, M. J. S.: Angew., Chem., Int. Ed. Engl. 10, 761 (1971); Zimmerman, H. E.: Acc. Chem. Res. 4, 272 (1971)

    Article  CAS  Google Scholar 

  28. Baggiolini, E., Schaffner, K., Jeger, O.: Chem. Commun. 1969, 1103

    Google Scholar 

  29. Turro, N. J., Dalton, J. C., Dawes, K., Farrington, G., Hautala, R., Morton, D., Niemczyk, M., Schore, N.: Acc. Chem. Res. 5, 92 (1972)

    Article  CAS  Google Scholar 

  30. Turro, N. J., Farneth, W. E., Devaquet, A.: J. Am. Chem. Soc. 98, 7425 (1976)

    CAS  Google Scholar 

  31. Quinkert has proposed a concerted mechanism for the photochemical ring expansion of cyclobutanones: Stohrer, W. D., Jacobs, P., Kaiser, K. H., Weich, G., Quinkert, G.: Top. Curr. Chem. 46, 181 (1974)

    CAS  Google Scholar 

  32. Salem, L.: J. Am. Chem. Soc., 96, 3486 (1974); Dauben, W. G., Salem, L., Turro, N. J.: Acc. Chem. Res. 8, 41 (1975)

    Article  CAS  Google Scholar 

  33. Hoffmann, R.: J. Am. Chem. Soc. 90, 1475 (1968)

    CAS  Google Scholar 

  34. Stephenson, L. M., Brauman, J. I.: J. Am. Chem. Soc. 93, 1988 (1971); Stephenson, L. M., Gibson, T. A., J. Am. Chem. Soc. 96, 5624 (1974)

    CAS  Google Scholar 

  35. Lewis, F. D., Hilliard, T. A.: J. Am. Chem. Soc. 94, 3852 (1972)

    CAS  Google Scholar 

  36. Agosta, W. C., Smith, A. B., III, Kende, A. S., Eilerman, R. G., Benham, J. Tetrahedron Lett. 1969, 4517; Agosta, W. C., Smith, A. B., III: J. Am. Chem. Soc. 93, 5513 (1971)

    Google Scholar 

  37. East, D. S. R., McMurray, T. B. H., Ratuakar, R.: J. Chem. Soc. Perkin I 1976, 433

    Google Scholar 

  38. Padwa, A., Ku, A., Sato, E.: Tetrahedron Lett. 1976, 2409

    Google Scholar 

  39. Herz, W., Iyer, V. S.: J. Org. Chem. 42, 1573 (1977)

    CAS  Google Scholar 

  40. Chapman, O. L., Kane, M., Lassila, J. D., Loeschen, R. L., Wright, H. E.: J. Am. Chem. Soc. 91, 6856 (1969)

    CAS  Google Scholar 

  41. Kende, A. S., Goldschmidt, Z., Izzo, P. I.: J. Am. Chem. Soc. 91, 6858 (1969)

    Article  CAS  Google Scholar 

  42. Quinkert, G.: Pure Appl. Chem. 33, 285 (1973)

    CAS  Google Scholar 

  43. Sasaki, T., Eguchi, S., Ohno, M.: J. Am. Chem. Soc. 92, 3192 (1970)

    Article  CAS  Google Scholar 

  44. Bonneau, R., Joussot-Dubien, J., Salem, L., Yarwood, A. J.: J. Am. Chem. Soc. 98, 4329 (1976); Bonneau, R., deViolet, P. F.: Compt. Rend. Acad. Sc. Paris Series C 284, 631 (1977)

    Article  CAS  Google Scholar 

  45. Lindberg, P., Bergman, R., Wickberg, B.: J. Chem. Soc. Chem. Commun. 1975, 946

    Google Scholar 

  46. For a discussion of cyclopropanone chemistry see Wassermann, H. H., Clark, G. M., Turley, P. C.: Topics Curr. Chem. 47, 73 (1974); Tilborg van, W. J. M., Steinberg, H., deBoer, T. H.: Rec. Trav. Chim. Pays-Bas 93, 294 (1974); Tilborg van, W. J. M.,: Thesis, University of Amsterdam 1971; Turro, N. J.: Acc. Chem. Res. 2, 25 (1969)

    Google Scholar 

  47. Wasserman, H. H., Baird, M. S.: Tetrahedron Lett. 1971, 3721

    Google Scholar 

  48. Wasserman, H. H., Hearn, M. H., Haveaux, B., Thyes, M.: J. Org. Chem. 41, 153 (1976)

    Article  CAS  Google Scholar 

  49. Koch, T. H., Howard, K. A.: Tetrahedron Lett. 1972, 4035

    Google Scholar 

  50. Howard, K. A., Koch, T. H.: J. Am. Chem. Soc. 97, 7288

    Google Scholar 

  51. Koch, T. H., Rodehorst, R. M.: Tetrahedron Lett. 1972, 4039

    Google Scholar 

  52. Rodehorst, R. M., Koch, T. H.: J. Am. Chem. Soc. 97, 7298 (1975)

    Article  CAS  Google Scholar 

  53. Gordon, A. J.: 14th Annual Report of Research of the Petroleum Research Fund, 1969,p. 185

    Google Scholar 

  54. Rawlings, D., Keute, J. S., Koch, T. H.: unpublished work

    Google Scholar 

  55. Beckett, A., Porter, G.: Trans. Faraday Soc. 59, 2051 (1963); Porter, G., Suppan, P.: Trans Faraday Soc. 61,1664(1965);Porter,G.,Suppan,P.: Trans. Faraday Soc. 62, 3375 (1966)

    CAS  Google Scholar 

  56. Baum, E. J., Wan, J. K. S., Pitts, Jr., J. N.: J. Am. Chem. Soc. 88, 2652 (1966); Pitts, Jr., J. N., Burley, D. R., Mani, J. C., Broadbent, A. D.: J. Am. Chem. Soc. 90, 5902 (1968)

    CAS  Google Scholar 

  57. Yang, N. C., McClure, D. S., Murov, S. L., Houser, J. J., Dusenbery, R.: J. Am. Chem. Soc. 89, 5466 (1967); Yang, N. C., Dusenbery, R.: J. Am. Chem. Soc. 90, 5899 (1968); Yang, N. C., Dusenbery, R.: Mol. Photochem. 1, 159 (1969)

    CAS  Google Scholar 

  58. Wagner, P. J., Capen, G.: Mol. Photochem. 1, 173 (1969); Wagner, P. J., Kamppainen, A. E., Schott, H. N.: J. Am. Chem. Soc. 95, 5604 (1973)

    CAS  Google Scholar 

  59. Anderson, D. R., Keute, J. S., Koch, T. H., Moseley, R. H.: J. Am. Chem. Soc. 99, 6332 (1977)

    CAS  Google Scholar 

  60. Keute, J. S., Koch, T. H.: unpublished work

    Google Scholar 

  61. Ullman, E. T., Singh, P.: J. Am. Chem. Soc. 94, 5077 (1972)

    CAS  Google Scholar 

  62. Weiss, D. S.: J. Photochem. 6, 301 (1977)

    Article  CAS  Google Scholar 

  63. Schuster, D. I., Barile, G. C., Liu, K.: J. Am. Chem. Soc. 97, 4441 (1975)

    CAS  Google Scholar 

  64. Turro, N. J., Dalton, J. C., Dawes, K. Farrington, G., Hautala, R., Morton, D., Niemczyk, M., Schore, N.: Acc. Chem. Res. 5, 92 (1972); Wolf, M. W., Legg, K. D., Brown, R. E., Singer, L. A., Parks, J. H.: J. Am. Chem. Soc. 97, 4490 (1975)

    Article  CAS  Google Scholar 

  65. Hochstrasser, R. M., Marzzacco, C. A. in Molecular Luminescence Lim, E. C. ed., New York: Benjamin, W. A.: 1969, p. 631

    Google Scholar 

  66. Arimoto, T., Osugi, J.: Chem. Lett. 1974, 271; Arimoto, T., Osugi, J.: Rev. Phys. Chem. Japan 44, 25 (1974)

    Google Scholar 

  67. Lewis, F. D., Hirsch, R. H., Roach, P. M., Johnson, D. E.: J. Am. Chem. Soc. 98, 8438 (1976); Schore, N. E., Turro, N. J., J. Am. Chem. Soc. 97, 2482 (1975)

    CAS  Google Scholar 

  68. Koch, T. H., Higgins, R. H., Schuster, H. F.: Tetrahedron Lett. 1977, 431

    Google Scholar 

  69. Hyatt, J. H., Swenton, J. S.: Chem. Comm. 1972, 1144; Swenton, J. S., Hyatt, J. H.: J. Am. Chem. Soc. 96, 4879 (1974)

    Google Scholar 

  70. Swenton, J. S., Balchunis, R. J.: J. Het. Chem. 11, 453 (1974); J. Het. Chem. 11, 917 (1974)

    CAS  Google Scholar 

  71. Tsuge, O., Oe, K., Tashiro, M.: Tetrahedron 29, 41 (1973)

    CAS  Google Scholar 

  72. Koch, T. H., Olesen, J. A., DeNiro, J.: J. Org. Chem. 40, 14 (1975)

    CAS  Google Scholar 

  73. Koch, T. H., Olesen, J., Foy, J.: J. Org. Chem. 40, 117 (1975)

    CAS  Google Scholar 

  74. Wharry, D., Koch, T. H.: unpublished work

    Google Scholar 

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Koch, T.H. et al. (1978). Photochemical reactivity of keto imino ethers. In: Organic Chemistry and Theory. Topics in Current Chemistry, vol 75. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0048836

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  • DOI: https://doi.org/10.1007/BFb0048836

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