Photodimerizations involving formation of eight-membered rings

  • Alexander Schönberg

Abstract

Naphthalene has hitherto not been reported to undergo photodimeri-zation but, according to Bradshaw and Hammond [1], 2-methoxynaphtha-lene (1) dimerizes upon irradiation with ultraviolet light in a variety of solvents. Other naphthalenes carrying methyl, hydroxy, bromo or amino substituents in the 1- or 2-positions resist photodimerization as does also 1-methoxynaphthalene. The photodimer from 1 was regarded to have the structure of a 5,8,9,12-tetrahydro-2,14- or 2,15-dimethyl-l,4[1’,4’]naph-thalenonaphthalene (syn or anti, 2 or 3).

Keywords

Mercury Benzene Recrystallization Naphthalene Diene 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    J. S. Bradshaw and G. S. Hammond: J. Amer. chem. Soc. 85, 3953 (1963).CrossRefGoogle Scholar
  2. [2]
    Fritzsche: J. Prakt. Chemie 101, 333 (1867).CrossRefGoogle Scholar
  3. [3]
    R. Luther and F. Weigert: Z. Physik. Chem. 51, 297 (1905).Google Scholar
  4. [4]
    N. S. Capper and J. K. Marsh: J. Chem. Soc. 1926, 724.Google Scholar
  5. [5]
    C. E. Linebarger: Am. Chem. J. 14, 597 (1892).Google Scholar
  6. [6]
    W. R. Orndorff and F. K. Cameron: Am. Chem. J. 17, 658 (1895).CrossRefGoogle Scholar
  7. [7]
    C. A. Coulson, L. E. Orgel, W. Taylor and J. Weiss: J. Chem. Soc. 1955, 2961.Google Scholar
  8. [8]
    E. J. Bowen and D. W. Tanner: Trans. Faraday Soc. 51, 475 (1955).CrossRefGoogle Scholar
  9. [9]
    R. Livingston : In: Photochemistry in the liquid and solid states. Ed. by L.J. Heidt, R. S. Livingston, E. Rabinowitch and F. Daniels, pp. 75–82. New York: Wiley 1960.Google Scholar
  10. [10]
    J. B. Birks and J. B. Aladekomo: Photochem. Photobiol. 2, 415 (1963).CrossRefGoogle Scholar
  11. [1]
    F. D. Greene, S. L. Misrock and J. R. Wolfe Jr.: J. Amer. chem. Soc. 77, 3852 (1955).CrossRefGoogle Scholar
  12. [12]
    R. Lalande and R. Calas: Bull. Soc. Chim. France 1960, 144.Google Scholar
  13. [13]
    D. E. Applequist, T. L. Brown, J. P. Kleiman and S. T. Young: Chem. and Ind. 1959, 850.Google Scholar
  14. [14]
    R. Calas, R. Lalande, J.-G. Faugère and F. Moulines: Bull. Soc. Chim. France 1965, 119.Google Scholar
  15. [15]
    D. E. Applequist, E. C. Friedrich and M. T. Rogers: J. Amer. chem. Soc. 81, 457 (1959).CrossRefGoogle Scholar
  16. [16]
    J.-G. Faugère and R. Calas: Comptes rendus 260, 585 [1965].Google Scholar
  17. [17]
    A. Willemart: Comptes rendus 205, 993 [1937].Google Scholar
  18. [18]
    A. Schönberg: Trans. Faraday Soc. 32, 514 [1936].CrossRefGoogle Scholar
  19. [19]
    F. D. Greene: Bull. Soc. Chim. France 1960, 1356.Google Scholar
  20. [20]
    C. H. Krauch and D. Hess: unpublished results.Google Scholar
  21. [21]
    R. Lalande, H. Bouas-Laurent and A. Cot: Bull. Soc. Chim. France 1965, 2695.Google Scholar
  22. [22]
    A. Schönberg, A. Mustafa, M. Z. Barakat, N. Latif, R. Moubasher and A. Mustafa: J. Chem. Soc. 1948, 2126.Google Scholar
  23. [23]
    A. Schönberg and A. Mustafa: J. Chem. Soc. 1949, 1039.Google Scholar
  24. [24]
    J. B. Birks, J. H. Appleyard and R. Pope: Photochem. Photobiol. 2, 493 (1963).CrossRefGoogle Scholar
  25. [25]
    E. C. Taylor and W. W. Paudler: Tetrahedron Letters 25, 1 [1960].CrossRefGoogle Scholar
  26. [26]
    W. A. Ayer, R. Hayatsu, P. De Mayo, S. T. Reid and J. B. Stothers: Tetrahedron Letters 1961, 648.Google Scholar
  27. [27]
    G. Slomp, F. A. MacKellar and L. A. Paquette: J. Amer. chem. Soc. 83, 4472 (1961).CrossRefGoogle Scholar
  28. [28]
    E. C. Taylor and R. O. Kan: J. Amer. chem. Soc. 85, 776 (1963).CrossRefGoogle Scholar
  29. [29]
    L. A. Paquette and G. Slomp: J. Amer. chem. Soc. 85, 765 (1963).CrossRefGoogle Scholar
  30. [30]
    A. Etienne: Comptes rendus 218, 841 (1944).Google Scholar
  31. [31]
    A. Etienne and A. Staehelin: Bull. Soc. Chim. France 1954, 748.Google Scholar
  32. [32]
    A. Etienne and M. Legrand: Comptes rendus 232, 1223 (1951).Google Scholar
  33. [33]
    A. Kellmann: J. Chim. Phys. 57, 468 (1957).Google Scholar
  34. [34]
    C. K. Bradsher, L. E. Beavers and J. H. Jones: J. Org. Chem. 22, 1740 [1957].CrossRefGoogle Scholar
  35. [35]
    P. De Mayo and R. W. Yip: Proc. Chem. Soc. 1964, 84.Google Scholar
  36. [36]
    A. Guyot and J. Catel: Bull. Soc. Chim. France [3] 35, 1124 (1906).Google Scholar
  37. [37]
    P. Courtot and D. H. Sachs: Bull. Soc. Chim. France 1965, 59.Google Scholar

Copyright information

© Springer-Verlag Berlin · Heidelberg 1968

Authors and Affiliations

  • Alexander Schönberg
    • 1
  1. 1.Technische Universität BerlinGermany

Personalised recommendations