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Arylated phenols, aroxyl radicals and aryloxenium ions syntheses and properties

  • Karl Dimroth
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 129)

Keywords

Phenol Derivative Phenoxyl Radical Lead Dioxide Potassium Hexacyanoferrate Pyrylium Salt 
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7 References

  1. 1.
    Methoden der Organischen Chemie, “Houben-Weyl” 4. edit. (ed. E. Müller), vol. VIc, part 1 and 2 (1976) Stuttgart, G. Thieme Verlag (cited later on only “Houben-Weyl”)Google Scholar
  2. 2.
    The Chemistry of the Hydroxyl group, part 1 and 2, ed. S. Patai, Interscience Publ., London, New York, Sidney, Toronto 1971Google Scholar
  3. 3.
    Bartlett, P. D., Roha, M., Stiles, R. M.: J. Am. Chem. Soc. 76, 2349 (1954)Google Scholar
  4. 3a.
    see also Hennion, G. F., Anderson, G. J.: ibid. 68, 424 (1946)Google Scholar
  5. 3b.
    Swanholm, U., Parker, V. D.: J. Chem. Soc. Perkin I, 1973, 562Google Scholar
  6. 4.
    Müller, E., Ley, K., Kiedaisch, W.: Chem. Ber. 87 1605 (1954)Google Scholar
  7. 5.
    Schlömer, K.: Dissertation Univ. Marburg 1959Google Scholar
  8. 6.
    Cook, C. D.: J. Org. Chem. 18, 261 (1953)Google Scholar
  9. 7.
    Müller, E., Ley, K.: Z. Naturforsch. 8b, 694 (1953)Google Scholar
  10. 8.
    Kalk, F.: Dissertation Univ. Marburg 1959 and unpublished resultsGoogle Scholar
  11. 9.
    Dimroth, K., Kalk, F., Neubauer, G.: Chem. Ber. 90, 2058 (1957)Google Scholar
  12. 10.
    Steuber, F. W., Dimroth, K.: ibid. 99, 258 (1966)Google Scholar
  13. 10a.
    Steuber, F. W.: Dissertation Univ. Marburg 1963. For a similar study with 2,6-di-t-butylated phenols see Šebesta, F., Petránek, J.: Coll. Czech. Chem. Commun. 35, 2136 (1970)Google Scholar
  14. 11.
    Cook, C. D., et al.: J. Am. Chem. Soc. 75, 6242 (1953); ibid. 81, 1176 (1959); J. Org. Chem. 29, 3716 (1964)Google Scholar
  15. 12.
    Müller, E., et al.: Chem. Ber. 87, 922 (1954); Liebigs Ann. Chem. 730, 67 (1969); see also Speiser, B., Rieker, A.: J. Electroanalyt. Chem. 102, 373 (1979)Google Scholar
  16. 13.
    Pummerer, R. et al.: I. Ber. dtsch. Chem. Ges. 47, 1472 (1914); XII. Chem. Ber. 86, 412 (1953)Google Scholar
  17. 14.
    Goldschmidt, St. et al.: Chem. Ber. 55, 3197 (1922); Liebigs Ann. Chem. 478, 1 (1930)Google Scholar
  18. 15.
    Coppinger, G. M.: J. Am. Chem. Soc. 79, 501 (1957); Tetrahedron 18, 61 (1962)Google Scholar
  19. 16.
    Kharasch, M. S., Joshi, B. S.: J. Org. Chem. 22, 1435, 1439 (1957), ibid. 27, 651 (1962)Google Scholar
  20. 17.
    Bartlett, P. D., Funahashi, T.: J. Am. Chem. Soc. 84, 2596 (1962); ibid. 88, 3303 (1966)Google Scholar
  21. 18.
    Pokhodenko, W. D., Kalibatschuk, N. N., Khizny, W. A.: Liebigs Ann. Chem. 743, 192 (1971)Google Scholar
  22. 19.
    Reviews of phenoxyl radicals: a. Altwicker, E. R.: Chem. Rev. 67, 475 (1967)Google Scholar
  23. 19. b.
    Forrester, A. R., Hay, J. M., Thomson, R. H.: Organic Chemistry of Stable Radicals Chapter 7; Academic Press London and New York 1968Google Scholar
  24. 19. c.
    Pokhodenko, V. D., Khizhnyi, V. A., Bidzilya, V. A.: Russ. Chem. Rev. (engl.) 37, 435 (1968)Google Scholar
  25. 19. d.
    Strigun, L. M., Vartanyan, L. S., Emanuel, N. M.: Russ. Chem. Rev. (engl.) 37, 421 (1968)Google Scholar
  26. 19. e.
    Pokhodenko, V. D.: Phenoxyl Radikals (russ.) Dumka Verlag Kiev 1969Google Scholar
  27. 19. f.
    Ershov, V. V., Volod'kin, A. A., Prokof'ev, A. I., Solodovnikov, S. P.: Russ. Chem. Rev. (engl.) 42, 740 (1973)Google Scholar
  28. 19. g.
    Vartanyan, L. S.: Russ. Chem. Rev. (engl.) 44, 859 (1975)Google Scholar
  29. 20.
    Hopff, H., Haer, A.: Chimia 12, 105 (1959); AgBF4-synthesis of acetophenone at 70–80° in 1,2-dichloromethane (23% yield): Crist, D. R., Hsieh, Z.-U., Chuicksall, C. O., Sun, M. K.: J. Org. Chem. 49, 2478 (1984)Google Scholar
  30. 21.
    Vorländer, D., Fischer, E., Wille, H.: Ber. Dtsch. Chem. Ges. 62, 2836 (1929)Google Scholar
  31. 22.
    Dimroth, K., Bräuninger, G.: Angew. Chem. 68, 519 (1956)Google Scholar
  32. 22a.
    Dimroth, K., Bräuninger, G., Neubauer, G.: Chem. Ber. 90, 1634 (1957)Google Scholar
  33. 22b.
    for electrophilic substitution of 1,3,5-triphenylbenzene see also Ansell, H. V., Clegg, R. B., Taylor, R.: J. Chem. Soc., Perkin II 1972, 766Google Scholar
  34. 23.
    Dimroth, K., Neubauer, G.: Angew. Chem. 69, 95 (1957)Google Scholar
  35. 24.
    Kohler, E. P., Blanchard, Jr., L. W.: J. Am. Chem. Soc. 57, 367 (1935)Google Scholar
  36. 25.
    Saure, M.: Dissertation Univ. Marburg 1959 and unpublished resultsGoogle Scholar
  37. 26.
    Lewis, G.: J. Org. chem. 30, 2798 (1965); ibid. 31, 749 (1966)Google Scholar
  38. 26a.
    Nowack, R.: unpublished results, Univ. Marburg 1962: The sulfonic acid of 1,3,5-triphenylbenzene with conc. H2SO4 in SO2 at −30–60 °C is the 4′-sulfonic acid, m.p. 84–85, giving the phenol 4′-hydroxy-1,3,5-benzene, m.p. 154–156 °C in molten KOH at 350 °CGoogle Scholar
  39. 27.
    Dimroth, K.: Angew. Chem. 72, 331 (1961)Google Scholar
  40. 27a.
    Dimroth, K., Wolf, K. H.: Newer Methods of Preparative Organic Chemistry, Vol. III, 357 (1964) (ed. W. Forest), Academic Press New YorkGoogle Scholar
  41. 28.
    Reviews: Balaban, A. T., Schroth, W., Fischer, G.: Adv. Heterocycl. Chem. 10, 241 (1969)Google Scholar
  42. 28a.
    Balaban, A. T., Dinculescu, A., Dorofeenko, G., Fischer, G., Koblik, A., Mezheritskii, M., Schroth, W.: ibid. Suppl. 2 (1982)Google Scholar
  43. 29.
    Reviews: Wedemeyer, K. F.: see lit. 1), 1e, 4–84Google Scholar
  44. 29a.
    Rawlinson, D. J., Sosnovski, G.: Synthesis 1972, 1–28; ibid. 1973, 567–603Google Scholar
  45. 29b.
    for methoxylation of arenes see Konz, E., Pistorius, R.: ibid. 1979, 603Google Scholar
  46. 29c.
    Groebel, B. T., Konz, E., Millauer, M., Pistorius, R.: ibid. 1979, 605Google Scholar
  47. 30.
    see e.g. Williams, G. H.: Homolytic Aromatic Substitution Pergamon Press Oxford 1960Google Scholar
  48. 31.
    Davidson, A. J., Norman, R. O. C.: J. Chem. Soc. (London) 1964, 5404Google Scholar
  49. 32.
    Eberson, L., Schäfer, H.: Top. Curr. Chem. 21, 1 (1971)Google Scholar
  50. 32a.
    Eberson, L., Nyberg, K.: Acc. Chem. Res. 6, 106 (1973)Google Scholar
  51. 32b.
    Eberson, L., Jönsson, L., Wistrand, L. G.: Tetrahedron 38, 1087 (1982)Google Scholar
  52. 32c.
    Eberson, L.: Adv. Phys. Organ. Chem. 18, 79 (1982)Google Scholar
  53. 32d.
    see also Enisov, E. T., Metelitsa, D. I.: Russ. Chem. Rev. (engl.) 37, 656 (1968)Google Scholar
  54. 33.
    Ross, S. D., Finkelstein, M., Petersen, R. C.: J. Am. Chem. Soc. 86, 4139 (1964)Google Scholar
  55. 33a.
    Leung, M., Herz, J., Salzberg, H. W.: J. Org. Chem. 30, 310, 2873 (1975)Google Scholar
  56. 33b.
    Adams, R. N.: Acc. Chem. Res. 2, 175 (1969)Google Scholar
  57. 34.
    Lund, H.: Acta Chem. Scand. 11, 1323 (1957)Google Scholar
  58. 35.
    Eberson, L., Nyberg, K.: ibid. 18, 1568 (1966) and lit. 36)Google Scholar
  59. 36.
    Eberson, L., Nyberg, K.: J. Am. Chem. Soc. 88, 1686 (1966); Eberson, L.: ibid. 89; 4669 (1967)Google Scholar
  60. 37.
    Blum, Z., Cedheim, L., Nyberg, K.: Acta Chem. Scand. B 29, 715 (1975)Google Scholar
  61. 38.
    So, Y. H., Miller, L. L.: Synthesis 1976, 468Google Scholar
  62. 39.
    Lau, W., Huffman, J. C., Kochi, J. K.: J. Am. Chem. Soc. 104, 5515 (1982); see also lit. 41)Google Scholar
  63. 40.
    Heiba, E. I., Dessau, R. M., Koehl Jr., W. J.: J. Am. Chem. Soc. 91, 6830 (1969)Google Scholar
  64. 41.
    Kochi, J. K., Tang, R. T., Bernath, T.: ibid. 95, 7114 (1973) and lit. cit. thereinGoogle Scholar
  65. 42.
    Nyberg, K., Wistrand, L.-G.: J. Org. Chem. 43, 2613 (1978)Google Scholar
  66. 42a.
    for catalysis see Eberson, L.: J. Mol. Catalys. 20, 27 (1983)Google Scholar
  67. 42b.
    Eberson, L., Jönsson, L.: Liebigs Ann. Chem. 1977, 233Google Scholar
  68. 43.
    Bell, H. C., Kalman, J. R., Pinhey, J. T., Sternhell, S.: Tetrahedron Lett. 1974, 853Google Scholar
  69. 43a.
    Kozyrod, R. P., Pinhey, J. T.: ibid. 23, 5365 (1982) and lit. cit. thereinGoogle Scholar
  70. 44.
    Eberson, L., Gomez-Gonzalez, L.: Acta Chem. Scand. 27, 1249 (1973)Google Scholar
  71. 44a.
    for similar acetoxylations see Eberson, L., Jönssen, L.: J. Chem. Soc. Chem. Commun. 1974, 885Google Scholar
  72. 44b.
    Eberson, L., Jönssen, L.: Acta Chem. Scand. B 28, 771 (1974); ibid. B 30, 361 (1976); Liebigs Ann. Chem. 1977, 233Google Scholar
  73. 44c.
    Jönssen, L.: Acta Chem. Scand. B 35, 683 (1981)Google Scholar
  74. 44d.
    Itahara, T.: Chem. and Ind. (London) 1982, 599Google Scholar
  75. 45.
    Baciocchi, E., Rol, C., Sebastini, G. V.: Gaz. Chim. Ital. 112, 513 (1982)Google Scholar
  76. 45a.
    Baciocchi, E., Mai, S., Rol, C., Mandolini, L.: J. Org. Chem. 43, 2919 (1978) and lit. cit. thereinGoogle Scholar
  77. 46.
    Matsuura, T., Omura, K.: Synthesis 1974, 173Google Scholar
  78. 47.
    Bachmann, W. E., Hoffmann, R. A.: Organic Reactions vol. 2, 224 (1944)Google Scholar
  79. 47a.
    Rüchardt, C., Merz, E.: Tetrahedron Letters 1964, 2431Google Scholar
  80. 47b.
    Weinberg, N. L., Weinberg, H. R.: Chem. Rev. 68, 449 (1968)Google Scholar
  81. 48.
    Hey, D. H., Williams, G. H.: in Rodd's Chemistry of Carbon Compounds, 2nd edit. vol. III, 119 (1971)Google Scholar
  82. 48a.
    Nonhebel, D. C., Walton, J. C.: Free Radical Chemistry 1974, p. 417, Cambridge University PressGoogle Scholar
  83. 48b.
    Minisci, F., Citterio in Adv. in Free Radical Chemistry, vol. 6, 65 (1980) (ed. G. H. Williams), Heyden, London, Philadelphia, RheineGoogle Scholar
  84. 48c.
    Sainsbury, M.: Tetrahedron 36, 3327 (1980)Google Scholar
  85. 49.
    Caronna, T., Ferrario, F., Servi, S.: Tetrahedron Lett. 1979, 657Google Scholar
  86. 50.
    Schromm, K.: Dissertation Univ. Marburg 1961Google Scholar
  87. 50a.
    Dimroth, K., Schromm, K.: unpublished results 1962Google Scholar
  88. 51.
    Kozyrod, R. P., Pinhey, J. T.: Tetrahedron Lett. 23, 1982, 5365 (1982)Google Scholar
  89. 52.
    Craig, H. C., Pinhey, J. T., Sternhell, S.: Aust. J. Chem. 32, 1551 (1979)Google Scholar
  90. 52a.
    Bell, H. C., May, G. L., Pinhey, J. T., Sternhell, S.: Tetrahedron Lett. 1976, 4303Google Scholar
  91. 53.
    Vollbracht, L., Bijkerk, A. H., Iedema, J.: USP 3413356; C. A. 70, 57402 (1969)Google Scholar
  92. 54.
    Intille, G.: USP 4008266; C. A. 86, 155349 (1977)Google Scholar
  93. 55.
    Barton, D. H. R., Blazejewski, J-C., Charpiot, B., Lester, D. J., Motherwell, W. B., Papoula, M. T. B.: J. Chem. Soc. Chem. Commun. 1980, 827Google Scholar
  94. 56.
    Endo, Y., Shudo, K., Okamoto, T.: J. Am. Chem. Soc. 99, 7721 (1977)Google Scholar
  95. 57.
    Wolf, W., Kharasch, N.: J. Org. Chem. 26, 283 (1961)Google Scholar
  96. 57a.
    Kharasch, N., Wolf, W., Erpelding, T. J., Naylor, P. G., Tokus, L.: Chem. and Ind. (London) 1962, 1720Google Scholar
  97. 57b.
    Wolf, W., Kharasch, N.: J. Org. Chem. 30, 2493 (1965)Google Scholar
  98. 57c.
    Photoarylation see also Soumillion, J. P., De Wolf, B.: Chem. Commun 1981, 436Google Scholar
  99. 57d.
    for iodophenolether synthesis see Burger, A., Wilson, E. L., Brindley, C. O., Bernheim, F.: J. Am. Chem. Soc. 67, 1416 (1945)Google Scholar
  100. 58.
    Ugochukwu, E. N., Wain, R. L.: Chem. and Ind. (London) 1965, 35Google Scholar
  101. 59.
    Schminke, H. D.: Dissertation Univ. Marburg 1961Google Scholar
  102. 60.
    Güsten, H., Kirsch, G., Schulte-Frohlinde, D.: Tetrahedron 24, 4393 (1968)Google Scholar
  103. 61.
    Hay, A., Clark, R. F.: Makromolecules 3, 533 (1970)Google Scholar
  104. 62.
    Gerard, W., Lappert, M. F.: Chem. Rev. 58, 1081 (1958)Google Scholar
  105. 62a.
    Schäfer, W., Franck, K.: Chem. Ber. 99, 160 (1966)Google Scholar
  106. 62b.
    McOmie, J. F., Watts, M. L., West, D. E.: Tetrahedron 24, 2289 (1968)Google Scholar
  107. 63.
    Adams, R., Mathieu, J.: J. Am. Chem. Soc. 70, 2120 (1948)Google Scholar
  108. 64.
    Prey, V.: Ber. Dtsch. Chem. Ges. 74, 1219 (1941); ibid. 75, 445 (1942); ibid. 76, 156 (1943)Google Scholar
  109. 65.
    Hazlet, S. E., Cory, R. A.: J. Org. Chem. 27, 2671 (1962)Google Scholar
  110. 66.
    Kolka, A. J., Napolitano, J. P., Filbey, A. H., Ecke, G. G.: ibid. 22, 642 (1957)Google Scholar
  111. 67.
    Smith, W., Sommerfield, E. H.: USP 4001340; C. A. 86, 120796 (1977)Google Scholar
  112. 67a.
    Britton, E. C.: USP 159283, (1931); C. 1934, II, 1688; USP 196744 (1932); C. 1935, II, 1962Google Scholar
  113. 67b.
    Moose, J. E.: USP 1979116 (1932); C 1935, I, 3200Google Scholar
  114. 68.
    Lüttringhaus, A., v. Sääf, G.: Angew. Chem. 51, 915 (1938); Liebigs Ann. Chem. 542, 241 (1939); 557, 25 (1947)Google Scholar
  115. 68a.
    Lüttringhaus, A., Ambros, D.: Chem. Ber. 89, 463 (1956)Google Scholar
  116. 69.
    Gilman, H., Esmay, D. L.: J. Am. Chem. Soc. 75, 2947 (1953)Google Scholar
  117. 69a.
    Gross, D. E., Fishel, N. A.: USP 4000203; C. A. 86, 89385 (1977)Google Scholar
  118. 69b.
    Gross, D. E.: USP 3989761; C. A. 86, 72193 (1977)Google Scholar
  119. 69c.
    Fishel, N. A., Gross, D. E.: USP 4035428; C. A. 87, 134 589 (1977)Google Scholar
  120. 69d.
    Fishel, N. A., Anvil, S. R., Gross, D. E.: Catalog Org. Synth. 1978, 119 (7th ed.)Google Scholar
  121. 69e.
    Müller, K. W.: USP 2862035; C. A. 53, 9157 (1959)Google Scholar
  122. 69f.
    Kagaku, S.: Jap. P. 81,20533, C. A. 95, 42640 91981)Google Scholar
  123. 69g.
    La Count, R. B., Friedman, S.: J. Org. Chem. 42, 2751 (1977)Google Scholar
  124. 69h.
    see also Squires, T. G., Vernier, C. G., Hodgson, B. A., Chung, L. W., Davies, V. A., Panuto, T. W.: J. Org. Chem. 46, 2373 (1981)Google Scholar
  125. 70.
    Bunnett, J. F., Zahler, R. E.: Chem. Rev. 49, 273 (1951)Google Scholar
  126. 70a.
    Davies, D. I., Hey, D. H., Williams, G. H.: J. Chem. Soc. (London) 1961, 562Google Scholar
  127. 71.
    Hawthorne, M. F.: J. Org. Chem. 22, 1001 (1957)Google Scholar
  128. 71a.
    Kuivila, H. G.: J. Am. Chem. Soc. 76, 870 (1954)Google Scholar
  129. 71b.
    Yarboro, T. L., Karr, C.: J. Org. Chem. 24, 1141 (1959)Google Scholar
  130. 72.
    Eberson, L., Jönsson, L., Wistrand, L.-G.: Tetrahedron 38, 1087 (1982) and lit. cit. thereinGoogle Scholar
  131. 73.
    Eberhardt, M. K.: J. Org. Chem. 42, 832 (1977); J. Phys. Chem. 81, 1051 (1977)Google Scholar
  132. 74.
    Zoratti, M., Bunnett, J. M.: J. Org. Chem. 45, 1769 (1980)Google Scholar
  133. 75.
    Bunnett, J. F.: Acc. Chem. Res. 11, 413 (1978)Google Scholar
  134. 76.
    Kornblum, N.: Angew. Chem. 87, 797 (1975); Angew. Chem. engl. 14, 734 (1975)Google Scholar
  135. 77a.
    Russell, G. A., Danen, W. C.: J. Am. Chem. Soc. 90, 347 (1968) and later publicationsGoogle Scholar
  136. 77b.
    Cerfontain, H.: J. Org. Chem. 47, 4680 (1982)Google Scholar
  137. 78.
    Suzumura, H.: Bl. chem. Soc. Japan 35, 108 (1962)Google Scholar
  138. 79.
    Hay, A. S., Clark, R. F.: Makromolecules 3, 533 (1970)Google Scholar
  139. 79a.
    Hay, A. S.: Fr. P. 1521 799; C. A. 71, 61006 (1969)Google Scholar
  140. 80.
    Plešek, J.: Chem. Listy 50, 246 (1956); C.A. 50, 7732 (1956) Coll. Czech. Chem. Commun. 21, 275 (1956)Google Scholar
  141. 80a.
    Munk, P., Plešek, J.: Chem. Listy 51, 771 (1957); C.A. 51, 11261 (1957)Google Scholar
  142. 80b.
    Plešek, J., Munk, P.: ibid. 51, 633 (1957)Google Scholar
  143. 80c.
    Munk, P., Plešek, J.: ibid 51, 771 (1957); C.A. 51, 11261 (1957)Google Scholar
  144. 80d.
    see also Kunze, H.: Ber. dtsch. Chem. Ges. 59, 2085 (1926)Google Scholar
  145. 80e.
    de Jonge, C. R. H. I., van Dort, H. M., Vollbracht, L.: Tetrahedron Lett. 1970, 1881Google Scholar
  146. 81.
    Hay, A. S.: Brit. P. 1207524 (1967); C.A. 77, 126220 (1967)Google Scholar
  147. 81a.
    Kapner, R. S., Kippax, D. L., Murphy, K. E., Udani, H. H.: Germ. P. 163402; C.A. 83, 163813 (1975)Google Scholar
  148. 81b.
    see also Brit. P. 1207524; C.A. 77, 126220 (1972)Google Scholar
  149. 82.
    Hay, A. S.: see lit. 61; Boon, J., Mayer, E. P.: J. Polymer Sci. 7, 205 (1969)Google Scholar
  150. 83.
    Schwarz, H. H., Metten, J., Koeller, H. Tacke, P., Weissel, O.: Germ. Offen 2.102746 (1971); C.A. 77 126218 (1972)Google Scholar
  151. 84.
    Naarman, H., Brandstetter, F., Schuster, H. H.: Europ. Appl. P. EP 47824; C.A. 96, 218455, 218418 (1982)Google Scholar
  152. 85a.
    Hay, A. S., Blanchard, H. S., Endres, G. F., Eustance, J. W.: J. Am. Chem. Soc. 81, 6335 (1959)Google Scholar
  153. 85b.
    see also Hay, A. S.: J. Org. Chem. 27, 3320 (1962); the Cu(I) complex is also very valuable for oxidative acetylene couplingGoogle Scholar
  154. 85c.
    Hay, A. S.: Tetrahedron Lett. 1965, 4241Google Scholar
  155. 86.
    Winnacker-Küchler: Chemische Technologie, 4. ed., vol. 6, Carl Hanser Verlag, München 1982Google Scholar
  156. 86a.
    Hay, A. S.: Advances Polymer Sci. 58, 581 (1962)Google Scholar
  157. 86b.
    Endres, G. F., Hay, A. S., Eustance, J. W.: J. Org. Chem. 28, 1300 (1963)Google Scholar
  158. 86c.
    X-ray of two cristalline poly-2,6-diphenyl-4-phenyl-oxydes see Boon, J., Magré, E. P.: Macromol. Chem. 136, 267 (1970)Google Scholar
  159. 87.
    Davies, G., El Sayed, M. A., Fasano, R. E.: Inorg. Chim. Acta 71, 95 (1983) and lit. cited thereinGoogle Scholar
  160. 87a.
    Capdevielle, P., Maumy, M.: Tetrahedron Lett. 24, 5611 (1983)Google Scholar
  161. 88.
    King, F. D., Walton, D. R. M.: Synthesis 1976, 40Google Scholar
  162. 89a.
    Pinhey, J. T., Rowe, B. A.: Aust. J. Chem. 33, 113 (1980)Google Scholar
  163. 89b.
    for other routes of α-arylation of ketons see: Bunnett, J. F., Sundberg J. E.: J. Org. Chem. 41, 1702 (1976) of potassium cyclohexanenolate in liquid ammonia with PhBr in benzene and light (350 nm) according to a SRN1 chain mechanism (72% 2-phenylcyclohexanone)Google Scholar
  164. 89c.
    Meerwein-α-arylation of cyclohexene-enolether or enolacetate with aryldiazonium salt and Cu(I) salts; Allard, M. N., Levisalle, J.: Bull. soc. chim. France 1972, 1926; Adel, Al., Salami, B. A., Levisalles, J., Rudler, H.: ibid. 1976, 930Google Scholar
  165. 89d.
    LiCuPh2 and p-tolyazocyclohexene: Sacks, C. E., Fuchs, P. L.: J. Am. Chem. Chem. Soc. 97, 7372 (1975)Google Scholar
  166. 89e.
    McKillop, A., Rao, D. P.: Syntheses 1977, 759Google Scholar
  167. 90.
    Krapcho, A. P., Lovey, A. J.: Tetrahedron Lett. 1973, 957Google Scholar
  168. 91.
    Barton, D. H. R., Papoula, H. T. B., Guilhem, J., Motherwell, W. B., Pascard, C., Huu Dau, E.: J. Chem, Soc. Chem. Commun. 1982, 732Google Scholar
  169. 91a.
    Barton, D. H. R., Lester, D. J. L., Motherwell, W., Papoula, M. T.: ibid. 1980, 246Google Scholar
  170. 92.
    Pinhey, J. T., Rowe, B. A.: Aust. J. Chem. 36, 789 (1983)Google Scholar
  171. 93.
    Horning, E. C., Horning, M. C.: J. Am. Chem. Soc. 69, 1359 (1947)Google Scholar
  172. 94.
    Woods, G. F., Tucker, I. W.: ibid 70, 2174 (1948)Google Scholar
  173. 95.
    Review: Posner, G. H.: Organic Reactions 19, 1 (1972)Google Scholar
  174. 96.
    Malmberg, H., Nilsson, M., Ullenius, C.: Tetrahedron Lett. 23, 3823 (1982); Review: Normant, J. F.: Synthesis 1972, 63Google Scholar
  175. 97.
    Woods, G. F., Reed, F. T., Arthur, T. E., Ezekiel, H.: J. Am. Chem. Soc. 73, 3854 (1951)Google Scholar
  176. 98.
    Petrow, A. D.: Ber. dtsch. Chem. Ges. 62, 642 (1929) and cited lit.; ibid. 63, 898 (1930)Google Scholar
  177. 99.
    Kenner, J., Shaw, H.: J. Chem. Soc. (London) 1931, 769Google Scholar
  178. 100.
    Sexsmith, D. R., Rassweiler, J. H.: J. Org. Chem. 25, 1229 (1960); see also lit. 99)Google Scholar
  179. 101. a)
    Downes, A. M., Gill, N. S., Lions, F.: J. Am. Chem. Soc. 72, 3464 (1951); for similar syntheses see b) Nasipuri, D., Roy Choudbury, S. R., Blattacharya, A.: J. Chem. Soc. Perkins I, 1973, 1451Google Scholar
  180. 102.
    Egli, C., Helali, S. E., Hardegger, E.: Helv. Chim. Acta 58, 104 (1975)Google Scholar
  181. 103.
    Zimmerman, H. E., Schuster, D. I.: J. Am. Chem. Soc. 84, 4527 (1962)Google Scholar
  182. 103a.
    for the syntheses of the 3,6-diphenyl-and 2,3-6-triphenyl-cyclohex-2-enones see Abdullah, S. M.: J. Ind. Chem. Soc., 12, 62 (1935); C. 1935 I, 3926Google Scholar
  183. 104.
    Hill, H. B.: Am Chem. J. 22, 89 (1899); 24, 5 (1900); Ber. dt. Chem. Ges. 33, 1241 (1900); see also Borsche, W.: Liebigs Ann. Chem. 312, 211 (1900)Google Scholar
  184. 105.
    Yates, P., Hyre, J. E.: J. Org. Chem. 27, 4101 (1962)Google Scholar
  185. 105a.
    for the synthesis of 2,3,4,6-and 2,3,5,6-tetraphenyl-phenol see also Eistert, B., Langbein, A.: Liebigs Ann. Chem. 678, 78 (1964)Google Scholar
  186. 106.
    Eicher, T., v. Angerer F. Lichigs Ann. 746, 120 (1971)Google Scholar
  187. 107.
    Ried, W., König, E.: ibid. 757, 153 (1972)Google Scholar
  188. 107a.
    see also Perst, H., Wesemeyer, I.: Tetrahedron Lett. 1970, 4189Google Scholar
  189. 108.
    Suter, C. M., Smith, P. G.: J. Am. Chem. Soc. 61, 166 (1939)Google Scholar
  190. 109.
    Ames, G. R., Davey, W.: J. Chem. Soc. London, 1957, 3480, 1958, 1794Google Scholar
  191. 109a.
    Betts, B. E., Davey, W.: ibid, 1961, 1683, 3440Google Scholar
  192. 109b.
    see also Fichter, F., Grether, E.: Ber. dtsch. Chem. Ges. 36, 1407 (1903)Google Scholar
  193. 110.
    Harrison Jr., E. A.: J. Org. Chem. 44, 1807 (1979)Google Scholar
  194. 111.
    Ueji, S., Nakatsu, K., Yoshioka, H., Kinoshita, K.: Tetrahedron Lett. 1982, 1173Google Scholar
  195. 112.
    Jones, E. C. S., Kenner, J.: J. chem. Soc. (London) 1931, 769; 1842Google Scholar
  196. 113.
    Hay, A. S.: J. Org. Chem. 30, 3577 (1965)Google Scholar
  197. 114.
    Bordwell, F. G., Wellmann, K. M.: ibid. 29, 509 (1964)Google Scholar
  198. 115.
    Worschech, K.: Dissertation Univ. Marburg 1960; see also lit. 137)Google Scholar
  199. 116.
    Kvalnes, D. E.: J. Am. Chem. Soc. 56, 2478 (1934)Google Scholar
  200. 117.
    Zimmerman, H. E.: Angew. Chem. 81, 45 (1969); engl. 8, 1Google Scholar
  201. 117a.
    Zimmerman, H. E., Epling, G. A.: J. Am. Chem. Soc. 94, 7806 (1972)Google Scholar
  202. 118.
    Dannenberg, W., Lemmer, D., Perst, H.: Tetrahedron Lett. 1974, 2133Google Scholar
  203. 118a.
    Dannenberg, W.: Dissertation Univ. Marburg 1975Google Scholar
  204. 118b.
    Rau, W.: Dipl. Arb. Univ. Marburg 1980Google Scholar
  205. 118c.
    the mechanism of these and similar rearrangements has been fully studied by Perst and coworkers, see e.g. Perst, H.: Habil. Arbeit, Univ. Marburg 1972Google Scholar
  206. 119.
    Dannenberg, W., Perst, H.: Liebigs Ann. Chem. 1975, 1873Google Scholar
  207. 119a.
    Dannenberg, W., Perst, H., Seifert, W. J.: Tetrahedron Lett. 1975, 3481Google Scholar
  208. 119b.
    Weisskopf, V., Perst, H.: Liebigs Ann. 1978, 1634Google Scholar
  209. 120.
    Monahan, A. S.: J. Org. Chem. 33, 1441 (1968)Google Scholar
  210. 121.
    Eistert, B., Langbein, A.: Liebigs Ann. Chem. 678, 78 (1964)Google Scholar
  211. 121a.
    Eistert, B., Thommen, A. J.: Chem. Ber. 104, 3048 (1971)Google Scholar
  212. 122.
    Dürr, H., Heilkämper, P.: Liebigs Ann. Chem. 716, 212 (1968)Google Scholar
  213. 123.
    Hart, H. Raggon, J. W.: Tetrahedron Lett. 24, 4891 (1983)Google Scholar
  214. 124.
    Evans, D. A., Hoffmann, J. M., Truesdale, L. K.: J. Am. Chem. Soc. 95, 5822 (1973)Google Scholar
  215. 124a.
    Evans, D. A., Hart, D. J., Koelsch, P. M., Chain, P. A.: Pure and Appl. Chem. 51, 1285 (1979) and lit. cit. thereinGoogle Scholar
  216. 124b.
    see also Parker, K. A., Kang, S.-K.: J. Org. Chem. 45, 1218 (1980)Google Scholar
  217. 125.
    Liotta, D., Saindane, M., Barnum, C.: J. Org. Chem. 46, 3369 (1981)Google Scholar
  218. 125a.
    Fischer, A., Henderson, G. N.: Tetrahedron Lett. 24, 131 (1983) and lit. cit. thereinGoogle Scholar
  219. 126.
    Rieker, A., Hernes, G.: Tetrahedron Lett. 1968, 3775Google Scholar
  220. 126a.
    Rieker, A.: Angew. Chem. 81, 938 (1969); engl. 8, 918 (1969)Google Scholar
  221. 127.
    Dimroth, K., Berndt, A., Volland, R.: Chem. Ber. 99, 3040 (1966)Google Scholar
  222. 127a.
    Berndt, A.: Dissertation Univ. Marburg 1965Google Scholar
  223. 128.
    Dimroth, K., Vogel, K., Krafft, W.: Chem. Ber. 101, 2215 (1968)Google Scholar
  224. 129.
    Michel, W.: Dissertation Univ. Marburg 1961Google Scholar
  225. 130.
    Müller, E., Schick, A., Scheffler, K.: Chem. Ber. 92, 474 (1959)Google Scholar
  226. 130a.
    Müller, E., Schick, A., Mayer, R., Scheffler, K.: ibid. 93, 2649 (1960)Google Scholar
  227. 131.
    Dimroth, K., Berndt, A., Reichardt, C.: Organic Synthesis, Coll. Vol. 5, 1128 (1973)Google Scholar
  228. 131a.
    Dimroth, K., Berndt, A., Perst, H., Reichardt, C.: ibid. p. 1130Google Scholar
  229. 131b.
    Dimroth, K., Reichardt, C., Vogel, K.: ibid. p. 1135Google Scholar
  230. 132.
    Blöcher, K. H.: Dissertation Univ. Marburg 1961Google Scholar
  231. 133.
    Dimroth, K., Kalk, F. Sell, R., Schlömer, K.: Liebigs Ann. Chem. 624, 51 (1959)Google Scholar
  232. 134.
    Dimroth, K., Wolf, K. H.: Angew. Chem. 72, 777 (1960)Google Scholar
  233. 135.
    Dimroth, K., Umbach, W., Blöcher, K. H.: Angew. Chem. 75, 860 (1963); Angew. Chem. engl. 2, 620 (1963) and unpublished results of Umbach, W.Google Scholar
  234. 136.
    Lendenfeld, H.: Monatsh. 27, 969 (1906); Ariyan, Z. S., Mooney, B.: J. Chem. Soc. (London) 1962, 1519Google Scholar
  235. 137.
    Wache, H.: Dissertation Univ. Marburg 1964Google Scholar
  236. 137a.
    Dimroth, K., Wache, H.: Chem. Ber. 99, 399 (1966)Google Scholar
  237. 138.
    Laubert, G.: Dissertation Univ. Marburg 1968Google Scholar
  238. 138a.
    Dimroth, K., Laubert, G., Blöcher, K. H.: Liebigs Ann. Chem. 765, 133 (1972)Google Scholar
  239. 139.
    Güsten, H., Kirsch, G., Schulte-Frohlinde, D.: Angew. Chem. 79, 941 (1967); engl. 6, 948 (1967); Tetrahedron 24, 4393 (1968)Google Scholar
  240. 140.
    Dimroth, K., Schromm, K.: unpublished results 1962Google Scholar
  241. 141.
    Nelsen, St. F.: in Free Radicals, (ed. J. K. Kochi) vol. II, 527, John Wiley and Sons, New York, London Sidney, Toronto (1973)Google Scholar
  242. 141a.
    Griller, D., Barclay, L. R., Ingold, K. U.: J. Am. Chem. Soc. 97, 6151 (1975) and lit. cited thereinGoogle Scholar
  243. 142.
    see also Chattaway, F. D., Orton, K. J. P.: J. Chem. Soc. (London) 79, 461 (1901)Google Scholar
  244. 142a.
    Goldschmidt, St.: Ber. dtsch. chem. Ges. 46, 2728 (1913)Google Scholar
  245. 143.
    see also Hedayatullah, M., Denivelle, L.: Compt. Rend. Acad. Sci. Paris 258, 5467 (1964); 259, 5516 (1965); Bull. Soc. Chim. France 1969, 4168Google Scholar
  246. 144.
    see also Schultz, G.: Ber. dtsch. chem. Ges. 17, 461 (1884)Google Scholar
  247. 145.
    Oosterloo, G.: Dissertation Univ. Marburg 1958Google Scholar
  248. 145a.
    Dimroth, K., Oosterloo, G.: Angew. Chem. 70, 165 (1958)Google Scholar
  249. 145b.
    2.4.6-Triphenylselenophenol see Kataeva, L. M., Kataev, E. T.: Zh. obć 32, 2712 (1962)Google Scholar
  250. 146.
    Dimroth, K., Kraft, K. J.: Angew. Chem. 76, 433 (1964); engl. 3, 384 (1964)Google Scholar
  251. 147. a)
    Kraft, K. J.: unpublished results, Univ. Marburg 1965Google Scholar
  252. 147. see also b)
    Porowska, N., Polaczkova, W., Kwiatowska, S.: some pk values in EtOH/H2O, Rocz. Chem. 44, 375 (1970); C. A. 72, 131888 (1970)Google Scholar
  253. 147. c)
    Bordwell, G. F., Mc Callum, R. J., Olmstead, W. N.: J. Org. Chem. 49, 1424 (1984)Google Scholar
  254. 148.
    Nakano, F., Sugishita, M.: Jap. P 74 40227; C.A. 82, 155 777 (1975).Google Scholar
  255. 149.
    Tacke, P.: Germ. Offen. 1930 341; C. A. 74, 87596 (1971); Smith N. E., Sommerfield, E. H.: USP 4001340; C.A. 86, 120976 (1977)Google Scholar
  256. 150.
    King, I. R., Hildon, A. M.: USP 4002693; C.A. 86, 120975 (1977)Google Scholar
  257. 151.
    Raychaudhuri, S. R.: Chem. and Ind. (London) 1980, 293Google Scholar
  258. 152.
    Kawamoto, A., Uda, H., Harada, N.: Bull. Chem. Soc. Japan 53, 3279 (1980)Google Scholar
  259. 153.
    Hay, A.: USP 3363008; C.A. 69, 2702 (1968)Google Scholar
  260. 154.
    Masamune, S., Casellucci, N. T.: J. Chem. Soc. (London), Proc. 1964, 298Google Scholar
  261. 155.
    Dürr, H.: Tetrahedron Lett. 1966, 5829; Liebigs Ann. Chem. 711, 115 (1968)Google Scholar
  262. 156.
    Farnum, D. G., Burr, M.: J. Am. Chem. Soc. 82, 2651 (1951)Google Scholar
  263. 157.
    Dana, D. E., Hay, A. S.: Synthesis 1982, 164: Improved synthesis and 4′, 4″ substituted derivatives, see also cited literatureGoogle Scholar
  264. 158.
    Plekhanova, L. G., Cuprova, N. A., Nikiforov, G. A., De Jonge, K., Golubeva, I. A., Ershov, V. V.: Izv. Akad. Nauk. SSSR, Ser Khim. 1980, 1656; C.A. 94, 3818 (1981): derivatives from 2,6-diphenylphenol by chloromethylation at C-4: CH2R: R=Cl, OMe, OEt, OH, H, and CH(CO2Et)2, CH2CO2HGoogle Scholar
  265. 159.
    Dimroth, K., Kaletsch, H.: unpubl. 1982 from (1) + CH2O and NaOH in EtOHGoogle Scholar
  266. 160.
    De Jonge, C. R. H., Hageman, H. J., Huysmans, W. B. G., Hijs, W. J.: J. Chem. Soc. (London), Perkin II, 1973, 1276Google Scholar
  267. 161.
    Stillson, G. H., Sawyer, D. W., Hunt, C. K.: J. Am. Chem. Soc. 67, 303 (1945)Google Scholar
  268. 161a.
    Müller, E., Schick, A., Scheffler, K.: Chem. Ber. 92, 474 (1959)Google Scholar
  269. 162.
    Müller, E., Schick, A., Mayer, R., Scheffler, K.: Chem. Ber. 93, 2649 (1960)Google Scholar
  270. 163.
    Hammel, D. E.: Dissertation Univ. Marburg 1964Google Scholar
  271. 164.
    Dimroth, K., Tüncher, W., Kaletsch, H.: Chem. Ber. 111, 264 (1978)Google Scholar
  272. 164a.
    Tüncher, W.: Dissertation Univ. Marburg 1976Google Scholar
  273. 165.
    Ristow, K. D.: Dissertation Univ. Marburg 1963; see also Webb, J. L., Hall, L.: US P 3739035; C.A. 79, 67035 (1973)Google Scholar
  274. 166.
    Umbach, W.: Dissertation Univ. Marburg 1962Google Scholar
  275. 167.
    Umbach, W., Dimroth, K.: 1963 not publishedGoogle Scholar
  276. 168.
    Müller, K. H.: Dissertation Univ. Marburg 1963Google Scholar
  277. 169.
    El-Kholy, I., Mishrikey, M. M., Rafla, F. K., Soliman, G.: J. Chem. Soc. (London), 1962 5153Google Scholar
  278. 169a.
    Ried, W., Kunkel, W., Strätz, A.: Liebigs Ann. Chem. 726, 69 (1969)Google Scholar
  279. 170.
    Musso, H., v. Grunelius, S.: Chem. Ber. 92, 3101 (1959)Google Scholar
  280. 170a.
    Barker, A. W., Kerlinger H, O., Shulgin, A. T.: Spectrochim. Acta 20, 1477 (1964)Google Scholar
  281. 171.
    Goddu, R. F.: J. Am. Chem. Soc. 82, 4533 (1960)Google Scholar
  282. 171a.
    Ingold, K. U., Taylor, D. R.: Can. J. Chem. 39, 471 (1961)Google Scholar
  283. 172.
    Hay, A. S., Boulette, B. M.: J. Org. Chem. 41, 1710 (1976)Google Scholar
  284. 173.
    Waters, W. A.: J. Chem. Soc. (London) B 1971, 2026Google Scholar
  285. 174.
    Allmann, R., Hellner, E.: Chem. Ber. 101, 2522 (1968)Google Scholar
  286. 175.
    For discussion see Rieker, A. in Houben-Weyl vol. VII 3b, part 2, p. 523 (1979)Google Scholar
  287. 176.
    Land, E. J., Porter, G., Strachan, E.: Trans. Faraday Soc. 57, 1885 (1961); 59, 2016 (1963)Google Scholar
  288. 177.
    Kuz'min, V. A., Khudjakov, I. V., Levin, Jr., P. P., Emmanuel, N. M., de Jonge, C. R. H.I., Hageman, H. J., Biemond, M. E. F., van der Maeden, F. P. B., Mijs, W. J.: J. Chem. Soc. Perkin II, 1979, 1540; 1981, 1234, 1237Google Scholar
  289. 177a.
    Burlatsky, S. F., Levin, P. P., Khudjakov, I. V., Kuzmin, V. A., Ovchinnikov, A. A.: Chem. Phys. Lett. 66, 565 (1979)Google Scholar
  290. 177b.
    for pulse radiolysis see also Neta, P.: J. Chem. Ed. 58, 110 (1981) for a short reviewGoogle Scholar
  291. 178.
    Ziegler, K., Ewald, L.: Liebigs Ann. Chem. 473, 163 (1929)Google Scholar
  292. 179.
    Dimroth, K., Berndt, A., Bär, F., Schweig, A., Volland, R.: Angew. Chem. 79, 69 (1967); engl. 6, 34 (1967)Google Scholar
  293. 180.
    Hyde, J. S.: J. Phys. Chem. 71, 68 (1967)Google Scholar
  294. 181.
    Cook, C. D., Depatie, C. B., English, E. S.: J. Org. Chem. 24, 1356 (1959)Google Scholar
  295. 182.
    Dimroth, K., Kraft, K. J.: Chem. Ber. 99, 264 (1966)Google Scholar
  296. 182a.
    Kraft, K. J.: Dissertation Univ. Marburg 1963Google Scholar
  297. 183.
    Braude, E. A., Brook, A. G., Linstead, R. P.: J. Chem. Soc. (London) 1954, 3569Google Scholar
  298. 183a.
    Part 13: Braude, E. A., Jackman, L. M., Linstead, R. P., Lowe, G.: ibid. 1960, 3133Google Scholar
  299. 183b.
    Reviews: Walker, D., Hiebert, J. H.: Chem. Rev. 67, 153 (1967)Google Scholar
  300. 183c.
    Jackman, L. M.: Adv. Organic Chem. vol. 2, 329 (1960); Interscience, New York.Google Scholar
  301. 183d.
    Half wave redox potential of DDCh in acetonitrile using dropping mercury electrode or a rotating platinum electrode and tetramethylammoniumperchlorate as supporting electrolyte have been found to be +0.51 V against a saturated standard calomel electrode: Peover, M. E.: J. Chem. Soc. (London) 1962, 4540Google Scholar
  302. 184.
    Nickel, B., Mauser, H., Hezel, U.: Z. Phys. Chem. N.F. 54, 196, 214 (1967)Google Scholar
  303. 184a.
    Mauser, H., Nickel, B.: Angew. Chem. 77, 378 (1965); engl. 4, 354 (1965).Google Scholar
  304. 185.
    Steenken, S.; Neta, P.: J. Phys. Chem. 86, 3661 (1982)Google Scholar
  305. 186.
    Gasanov, B. R., Stradyn', Y. P.: J. Gen. Chem. of USSR, engl. 46, 2469 (1976)Google Scholar
  306. 187.
    Müller, E., Rieker, A., Schick, A.: Liebigs Ann. Chem. 673, 40 (1964)Google Scholar
  307. 187a.
    Rieker, A.: Chem. Ber. 98, 715 (1965)Google Scholar
  308. 187b.
    Becker, H.-D.: J. Org. Chem. 29, 3068 (1964); 30, 982 (1965)Google Scholar
  309. 188.
    Dimroth, K., Berndt, H.: Chem. Ber. 101, 2519 (1968)Google Scholar
  310. 189.
    Dimroth, K., Tüncher, W.: Synthesis 1977, 339Google Scholar
  311. 190.
    Haaß, K.: Dissertation Univ. Marburg 1962Google Scholar
  312. 191.
    Criegée, R.: Ber. dtsch. Chem. Ges. 69, 2758 (1936)Google Scholar
  313. 192a.
    Reviews: Zollinger, H.: Angew. Chem. 70, 204 (1958)Google Scholar
  314. 192b.
    Krumbiegl, P.: Isotopieeffekte, Akademie Verlag, Berlin 1970Google Scholar
  315. 193a.
    Hageman, H. J., Huysmans, W. G. B.: J. Chem. Soc. Chem. Commun. 1969, 837.Google Scholar
  316. 193b.
    For similar reactions by heating 2,6,2′,6′-tetraphenyldiphenoquinone see Hay, A. S.: J. Org. Chem. 36, 218 (1971)Google Scholar
  317. 194.
    Sviridov, B. D., Gyzunova, L. P., Kuznetz, V. M., Nikiforov, G. A., De Jonge, K., Hageman, H. J., Ershov, V. V.: Izv. Akad. Nauk SSSR, Ser. Khim. 9, 2160 (1978); (C.A. 90, 21981 (1979)Google Scholar
  318. 195a.
    Reviews: Rotermund, G. W.: Houben Weyl IV 1b, 761 (1975)Google Scholar
  319. 195b.
    Wedemeyer, K. F.: ibid. VI 1c, (1976)Google Scholar
  320. 195c.
    Ulrich, H., Richter, R.: ibid, VII 3a, 27 (1977)Google Scholar
  321. 195d.
    Boldt, P.: ibid. VII 3a, 27 (1977)Google Scholar
  322. 195e.
    Barton, D. H. R.: Chem. in Britain 3, 330 (1967) and lit. cit. thereinGoogle Scholar
  323. 195f.
    Musso, H.: Angew. Chem. 75, 965 (1963)Google Scholar
  324. 195g.
    see also Bird, C. W., Chauhan, Y.-P.: Tetrahedron Lett. 1978, 2133Google Scholar
  325. 196.
    Teuber, H. J., Glossauer, G.: Chem. Ber. 98, 2643 (1965)Google Scholar
  326. 197a.
    De Jonge, C. R. H. I., van Dort, H. M., Vollbracht, L.: Tetrahedron Lett. 1970, 1981; see cit. ref. for oxidation of phenols in apolar solventsGoogle Scholar
  327. 197b.
    Finkbeiner, H., Toothacker, A. T.: J. Org. Chem. 33, 4347 (1965)Google Scholar
  328. 198.
    Dewar, M. J. S., Nakaya, T.: J. Am. Chem. Soc. 90, 7134 (1968)Google Scholar
  329. 199.
    Vogt Jr., L. H., Wirth, J. G., Finkbeiner, H. L.: J. Org. Chem. 34, 273 (1969)Google Scholar
  330. 200.
    Bolton, D. A.: ibid. 34, 2031 (1969)Google Scholar
  331. 201a.
    Abramovitch, R. A., Alvernhe, G., Bartnik, R., Dassanayake, N. L., Inbasekaran, M. N., Kato, S.: J. Am. Chem. Soc. 103, 4558 (1981) and lit. cited thereinGoogle Scholar
  332. 201b.
    Martius, C., Eilingsfeld, H.: Liebigs Ann. Chem. 607, 159 (1957)Google Scholar
  333. 201c.
    Adler, E., Falkehag, I., Smith, B.: Acta Chim. Scand. 16, 529 (1962)Google Scholar
  334. 202.
    Suttie, A. B.: Tetrahedron Lett. 1969, 953Google Scholar
  335. 203a.
    Rolán, A., Parker, V. D.: J. Chem. Soc. (London) (C) 1971, 3214Google Scholar
  336. 203b.
    Rolán, A.: J. Chem. Soc., Chem. Commun. 1971, 1643Google Scholar
  337. 203c.
    Nilsson, A., Palmquist, U., Pettersson, T., Rolán, A.: (part 5), J. Chem. Soc. (London), Perkin I, 1978, 696 and lit. cit. thereinGoogle Scholar
  338. 203d.
    Rieker, A., Dreher, E.-L., Geisel, H., Khalifa, M. H.: Syntheses 1978, 851Google Scholar
  339. 203e.
    Speiser, B., Rieker, A.: J. Elektrol. Chem. 110, 231 (1980)Google Scholar
  340. 203f.
    Review: Evans, D. H.: Acc. Chem. Res. 10, 313 (1977)Google Scholar
  341. 204.
    Rieker, A., Bracht, J., Dreher, E. L., Schneider, P.: Houben-Weyl, vol. VII 3b, 529 (1979)Google Scholar
  342. 205.
    Dimroth, K., Umbach, W., Thomas, H.: Chem. Ber. 100, 132 (1967), see also ref. 166)Google Scholar
  343. 206a.
    Dimroth, K., Thomas, H.: Chem. Ber. 102, 3795 (1969)Google Scholar
  344. 206b.
    Thomas, H.: Dissertation Univ. Marburg 1968Google Scholar
  345. 207a.
    Abramovitch, R. A., Bartnik, R., Cooper, M., Dassanayake, N. L., Hwang, H.-Y., Inbasekaran, M. N., Rusek, G.: J. Org. Chem. 47, 4817 (1982) and ref. cit. therein.Google Scholar
  346. 207b.
    For a related coupling reaction of phenol with hypervalent iodine (III) species see White, J. D., Chong, W. K. M., Thirring, K.: J. Org. Chem. 48, 2300 (1983)Google Scholar
  347. 208a.
    Wessely, F., Sinwel, F.: Monatsh. Chem. 81, 1055 (1950)Google Scholar
  348. 208b.
    Dimroth, K., Perst, H., Schlömer, K., Worschech, K., Müller, K.-H.: Chem. Ber. 100, 629 (1967)Google Scholar
  349. 209.
    Rieker, A., Rundel, W., Kessler, H.: Z. Natforsch. 24b, 547 (1969)Google Scholar
  350. 210.
    Sell, R.: Dissertation Universität Marburg 1960; see also ref. 133)Google Scholar
  351. 211.
    Dimroth, K., Perst, H.: Liebigs Ann. Chem. 708, 86 (1967), see also Perst, H.: Dissertation Universität Marburg 1965Google Scholar
  352. 212.
    Dimroth, K., Perst, H., Müller, K.-H.: Chem. Ber. 100, 1850 (1967); see also ref. 168)Google Scholar
  353. 213.
    Zbiral, E., Wessely, F., Lahrmann, L.: Monatsh. Chem. 91, 92 (1960)Google Scholar
  354. 214.
    Nishinaga, A., Itahara, T., Matsuura, T., Berger, S., Henes, G., Rieker, A.: Chem. Ber. 109, 1530 (1976)Google Scholar
  355. 215.
    Perst, H., Dimroth, K.: Tetrahedron 24, 5385 (1968)Google Scholar
  356. 216a.
    Perst, H., Sprenger, W.: Tetrahedron Lett. 1970, 3601Google Scholar
  357. 216b.
    Perst, H., Wesemeier, I.: ibid. 1970, 4189Google Scholar
  358. 216c.
    Lemmer, D., Perst, H.: ibid. 1972, 2735Google Scholar
  359. 216d.
    Seifert, W. J., Perst, H., Dannenberg, W.: ibid. 1973, 4999Google Scholar
  360. 216e.
    Seifert, W., Perst H.: ibid. 1975, 2419Google Scholar
  361. 216f.
    Dannenberg, W., Seifert, W. J., Perst, H.: ibid. 1975, 3481Google Scholar
  362. 216g.
    Perst, H., Dannenberg, W.: Liebigs Ann. Chem. 1975, 1873Google Scholar
  363. 216h.
    Weisskopf, V., Perst, H.: Liebigs Ann. Chem. 1978, 1634Google Scholar

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© Springer-Verlag 1985

Authors and Affiliations

  • Karl Dimroth
    • 1
  1. 1.Fachbereich Chemie der UniversitätMarburgFRG

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