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Arylated phenols, aroxyl radicals and aryloxenium ions syntheses and properties

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Photochemistry and Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 129))

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7 References

  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. The Chemistry of the Hydroxyl group, part 1 and 2, ed. S. Patai, Interscience Publ., London, New York, Sidney, Toronto 1971

    Google Scholar 

  3. Bartlett, P. D., Roha, M., Stiles, R. M.: J. Am. Chem. Soc. 76, 2349 (1954)

    Google Scholar 

  4. see also Hennion, G. F., Anderson, G. J.: ibid. 68, 424 (1946)

    Google Scholar 

  5. Swanholm, U., Parker, V. D.: J. Chem. Soc. Perkin I, 1973, 562

    Google Scholar 

  6. Müller, E., Ley, K., Kiedaisch, W.: Chem. Ber. 87 1605 (1954)

    Google Scholar 

  7. Schlömer, K.: Dissertation Univ. Marburg 1959

    Google Scholar 

  8. Cook, C. D.: J. Org. Chem. 18, 261 (1953)

    Google Scholar 

  9. Müller, E., Ley, K.: Z. Naturforsch. 8b, 694 (1953)

    Google Scholar 

  10. Kalk, F.: Dissertation Univ. Marburg 1959 and unpublished results

    Google Scholar 

  11. Dimroth, K., Kalk, F., Neubauer, G.: Chem. Ber. 90, 2058 (1957)

    Google Scholar 

  12. Steuber, F. W., Dimroth, K.: ibid. 99, 258 (1966)

    Google Scholar 

  13. 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. 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. 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. Pummerer, R. et al.: I. Ber. dtsch. Chem. Ges. 47, 1472 (1914); XII. Chem. Ber. 86, 412 (1953)

    Google Scholar 

  17. Goldschmidt, St. et al.: Chem. Ber. 55, 3197 (1922); Liebigs Ann. Chem. 478, 1 (1930)

    Google Scholar 

  18. Coppinger, G. M.: J. Am. Chem. Soc. 79, 501 (1957); Tetrahedron 18, 61 (1962)

    Google Scholar 

  19. Kharasch, M. S., Joshi, B. S.: J. Org. Chem. 22, 1435, 1439 (1957), ibid. 27, 651 (1962)

    Google Scholar 

  20. Bartlett, P. D., Funahashi, T.: J. Am. Chem. Soc. 84, 2596 (1962); ibid. 88, 3303 (1966)

    Google Scholar 

  21. Pokhodenko, W. D., Kalibatschuk, N. N., Khizny, W. A.: Liebigs Ann. Chem. 743, 192 (1971)

    Google Scholar 

  22. Reviews of phenoxyl radicals: a. Altwicker, E. R.: Chem. Rev. 67, 475 (1967)

    Google Scholar 

  23. Forrester, A. R., Hay, J. M., Thomson, R. H.: Organic Chemistry of Stable Radicals Chapter 7; Academic Press London and New York 1968

    Google Scholar 

  24. Pokhodenko, V. D., Khizhnyi, V. A., Bidzilya, V. A.: Russ. Chem. Rev. (engl.) 37, 435 (1968)

    Google Scholar 

  25. Strigun, L. M., Vartanyan, L. S., Emanuel, N. M.: Russ. Chem. Rev. (engl.) 37, 421 (1968)

    Google Scholar 

  26. Pokhodenko, V. D.: Phenoxyl Radikals (russ.) Dumka Verlag Kiev 1969

    Google Scholar 

  27. Ershov, V. V., Volod'kin, A. A., Prokof'ev, A. I., Solodovnikov, S. P.: Russ. Chem. Rev. (engl.) 42, 740 (1973)

    Google Scholar 

  28. Vartanyan, L. S.: Russ. Chem. Rev. (engl.) 44, 859 (1975)

    Google Scholar 

  29. 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. Vorländer, D., Fischer, E., Wille, H.: Ber. Dtsch. Chem. Ges. 62, 2836 (1929)

    Google Scholar 

  31. Dimroth, K., Bräuninger, G.: Angew. Chem. 68, 519 (1956)

    Google Scholar 

  32. Dimroth, K., Bräuninger, G., Neubauer, G.: Chem. Ber. 90, 1634 (1957)

    Google Scholar 

  33. for electrophilic substitution of 1,3,5-triphenylbenzene see also Ansell, H. V., Clegg, R. B., Taylor, R.: J. Chem. Soc., Perkin II 1972, 766

    Google Scholar 

  34. Dimroth, K., Neubauer, G.: Angew. Chem. 69, 95 (1957)

    Google Scholar 

  35. Kohler, E. P., Blanchard, Jr., L. W.: J. Am. Chem. Soc. 57, 367 (1935)

    Google Scholar 

  36. Saure, M.: Dissertation Univ. Marburg 1959 and unpublished results

    Google Scholar 

  37. Lewis, G.: J. Org. chem. 30, 2798 (1965); ibid. 31, 749 (1966)

    Google Scholar 

  38. 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 °C

    Google Scholar 

  39. Dimroth, K.: Angew. Chem. 72, 331 (1961)

    Google Scholar 

  40. Dimroth, K., Wolf, K. H.: Newer Methods of Preparative Organic Chemistry, Vol. III, 357 (1964) (ed. W. Forest), Academic Press New York

    Google Scholar 

  41. Reviews: Balaban, A. T., Schroth, W., Fischer, G.: Adv. Heterocycl. Chem. 10, 241 (1969)

    Google Scholar 

  42. Balaban, A. T., Dinculescu, A., Dorofeenko, G., Fischer, G., Koblik, A., Mezheritskii, M., Schroth, W.: ibid. Suppl. 2 (1982)

    Google Scholar 

  43. Reviews: Wedemeyer, K. F.: see lit. 1), 1e, 4–84

    Google Scholar 

  44. Rawlinson, D. J., Sosnovski, G.: Synthesis 1972, 1–28; ibid. 1973, 567–603

    Google Scholar 

  45. for methoxylation of arenes see Konz, E., Pistorius, R.: ibid. 1979, 603

    Google Scholar 

  46. Groebel, B. T., Konz, E., Millauer, M., Pistorius, R.: ibid. 1979, 605

    Google Scholar 

  47. see e.g. Williams, G. H.: Homolytic Aromatic Substitution Pergamon Press Oxford 1960

    Google Scholar 

  48. Davidson, A. J., Norman, R. O. C.: J. Chem. Soc. (London) 1964, 5404

    Google Scholar 

  49. Eberson, L., Schäfer, H.: Top. Curr. Chem. 21, 1 (1971)

    Google Scholar 

  50. Eberson, L., Nyberg, K.: Acc. Chem. Res. 6, 106 (1973)

    Google Scholar 

  51. Eberson, L., Jönsson, L., Wistrand, L. G.: Tetrahedron 38, 1087 (1982)

    Google Scholar 

  52. Eberson, L.: Adv. Phys. Organ. Chem. 18, 79 (1982)

    Google Scholar 

  53. see also Enisov, E. T., Metelitsa, D. I.: Russ. Chem. Rev. (engl.) 37, 656 (1968)

    Google Scholar 

  54. Ross, S. D., Finkelstein, M., Petersen, R. C.: J. Am. Chem. Soc. 86, 4139 (1964)

    Google Scholar 

  55. Leung, M., Herz, J., Salzberg, H. W.: J. Org. Chem. 30, 310, 2873 (1975)

    Google Scholar 

  56. Adams, R. N.: Acc. Chem. Res. 2, 175 (1969)

    Google Scholar 

  57. Lund, H.: Acta Chem. Scand. 11, 1323 (1957)

    Google Scholar 

  58. Eberson, L., Nyberg, K.: ibid. 18, 1568 (1966) and lit. 36)

    Google Scholar 

  59. Eberson, L., Nyberg, K.: J. Am. Chem. Soc. 88, 1686 (1966); Eberson, L.: ibid. 89; 4669 (1967)

    Google Scholar 

  60. Blum, Z., Cedheim, L., Nyberg, K.: Acta Chem. Scand. B 29, 715 (1975)

    Google Scholar 

  61. So, Y. H., Miller, L. L.: Synthesis 1976, 468

    Google Scholar 

  62. Lau, W., Huffman, J. C., Kochi, J. K.: J. Am. Chem. Soc. 104, 5515 (1982); see also lit. 41)

    Google Scholar 

  63. Heiba, E. I., Dessau, R. M., Koehl Jr., W. J.: J. Am. Chem. Soc. 91, 6830 (1969)

    Google Scholar 

  64. Kochi, J. K., Tang, R. T., Bernath, T.: ibid. 95, 7114 (1973) and lit. cit. therein

    Google Scholar 

  65. Nyberg, K., Wistrand, L.-G.: J. Org. Chem. 43, 2613 (1978)

    Google Scholar 

  66. for catalysis see Eberson, L.: J. Mol. Catalys. 20, 27 (1983)

    Google Scholar 

  67. Eberson, L., Jönsson, L.: Liebigs Ann. Chem. 1977, 233

    Google Scholar 

  68. Bell, H. C., Kalman, J. R., Pinhey, J. T., Sternhell, S.: Tetrahedron Lett. 1974, 853

    Google Scholar 

  69. Kozyrod, R. P., Pinhey, J. T.: ibid. 23, 5365 (1982) and lit. cit. therein

    Google Scholar 

  70. Eberson, L., Gomez-Gonzalez, L.: Acta Chem. Scand. 27, 1249 (1973)

    Google Scholar 

  71. for similar acetoxylations see Eberson, L., Jönssen, L.: J. Chem. Soc. Chem. Commun. 1974, 885

    Google Scholar 

  72. Eberson, L., Jönssen, L.: Acta Chem. Scand. B 28, 771 (1974); ibid. B 30, 361 (1976); Liebigs Ann. Chem. 1977, 233

    Google Scholar 

  73. Jönssen, L.: Acta Chem. Scand. B 35, 683 (1981)

    Google Scholar 

  74. Itahara, T.: Chem. and Ind. (London) 1982, 599

    Google Scholar 

  75. Baciocchi, E., Rol, C., Sebastini, G. V.: Gaz. Chim. Ital. 112, 513 (1982)

    Google Scholar 

  76. Baciocchi, E., Mai, S., Rol, C., Mandolini, L.: J. Org. Chem. 43, 2919 (1978) and lit. cit. therein

    Google Scholar 

  77. Matsuura, T., Omura, K.: Synthesis 1974, 173

    Google Scholar 

  78. Bachmann, W. E., Hoffmann, R. A.: Organic Reactions vol. 2, 224 (1944)

    Google Scholar 

  79. Rüchardt, C., Merz, E.: Tetrahedron Letters 1964, 2431

    Google Scholar 

  80. Weinberg, N. L., Weinberg, H. R.: Chem. Rev. 68, 449 (1968)

    Google Scholar 

  81. Hey, D. H., Williams, G. H.: in Rodd's Chemistry of Carbon Compounds, 2nd edit. vol. III, 119 (1971)

    Google Scholar 

  82. Nonhebel, D. C., Walton, J. C.: Free Radical Chemistry 1974, p. 417, Cambridge University Press

    Google Scholar 

  83. Minisci, F., Citterio in Adv. in Free Radical Chemistry, vol. 6, 65 (1980) (ed. G. H. Williams), Heyden, London, Philadelphia, Rheine

    Google Scholar 

  84. Sainsbury, M.: Tetrahedron 36, 3327 (1980)

    Google Scholar 

  85. Caronna, T., Ferrario, F., Servi, S.: Tetrahedron Lett. 1979, 657

    Google Scholar 

  86. Schromm, K.: Dissertation Univ. Marburg 1961

    Google Scholar 

  87. Dimroth, K., Schromm, K.: unpublished results 1962

    Google Scholar 

  88. Kozyrod, R. P., Pinhey, J. T.: Tetrahedron Lett. 23, 1982, 5365 (1982)

    Google Scholar 

  89. Craig, H. C., Pinhey, J. T., Sternhell, S.: Aust. J. Chem. 32, 1551 (1979)

    Google Scholar 

  90. Bell, H. C., May, G. L., Pinhey, J. T., Sternhell, S.: Tetrahedron Lett. 1976, 4303

    Google Scholar 

  91. Vollbracht, L., Bijkerk, A. H., Iedema, J.: USP 3413356; C. A. 70, 57402 (1969)

    Google Scholar 

  92. Intille, G.: USP 4008266; C. A. 86, 155349 (1977)

    Google Scholar 

  93. 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, 827

    Google Scholar 

  94. Endo, Y., Shudo, K., Okamoto, T.: J. Am. Chem. Soc. 99, 7721 (1977)

    Google Scholar 

  95. Wolf, W., Kharasch, N.: J. Org. Chem. 26, 283 (1961)

    Google Scholar 

  96. Kharasch, N., Wolf, W., Erpelding, T. J., Naylor, P. G., Tokus, L.: Chem. and Ind. (London) 1962, 1720

    Google Scholar 

  97. Wolf, W., Kharasch, N.: J. Org. Chem. 30, 2493 (1965)

    Google Scholar 

  98. Photoarylation see also Soumillion, J. P., De Wolf, B.: Chem. Commun 1981, 436

    Google Scholar 

  99. for iodophenolether synthesis see Burger, A., Wilson, E. L., Brindley, C. O., Bernheim, F.: J. Am. Chem. Soc. 67, 1416 (1945)

    Google Scholar 

  100. Ugochukwu, E. N., Wain, R. L.: Chem. and Ind. (London) 1965, 35

    Google Scholar 

  101. Schminke, H. D.: Dissertation Univ. Marburg 1961

    Google Scholar 

  102. Güsten, H., Kirsch, G., Schulte-Frohlinde, D.: Tetrahedron 24, 4393 (1968)

    Google Scholar 

  103. Hay, A., Clark, R. F.: Makromolecules 3, 533 (1970)

    Google Scholar 

  104. Gerard, W., Lappert, M. F.: Chem. Rev. 58, 1081 (1958)

    Google Scholar 

  105. Schäfer, W., Franck, K.: Chem. Ber. 99, 160 (1966)

    Google Scholar 

  106. McOmie, J. F., Watts, M. L., West, D. E.: Tetrahedron 24, 2289 (1968)

    Google Scholar 

  107. Adams, R., Mathieu, J.: J. Am. Chem. Soc. 70, 2120 (1948)

    Google Scholar 

  108. Prey, V.: Ber. Dtsch. Chem. Ges. 74, 1219 (1941); ibid. 75, 445 (1942); ibid. 76, 156 (1943)

    Google Scholar 

  109. Hazlet, S. E., Cory, R. A.: J. Org. Chem. 27, 2671 (1962)

    Google Scholar 

  110. Kolka, A. J., Napolitano, J. P., Filbey, A. H., Ecke, G. G.: ibid. 22, 642 (1957)

    Google Scholar 

  111. Smith, W., Sommerfield, E. H.: USP 4001340; C. A. 86, 120796 (1977)

    Google Scholar 

  112. Britton, E. C.: USP 159283, (1931); C. 1934, II, 1688; USP 196744 (1932); C. 1935, II, 1962

    Google Scholar 

  113. Moose, J. E.: USP 1979116 (1932); C 1935, I, 3200

    Google Scholar 

  114. Lüttringhaus, A., v. Sääf, G.: Angew. Chem. 51, 915 (1938); Liebigs Ann. Chem. 542, 241 (1939); 557, 25 (1947)

    Google Scholar 

  115. Lüttringhaus, A., Ambros, D.: Chem. Ber. 89, 463 (1956)

    Google Scholar 

  116. Gilman, H., Esmay, D. L.: J. Am. Chem. Soc. 75, 2947 (1953)

    Google Scholar 

  117. Gross, D. E., Fishel, N. A.: USP 4000203; C. A. 86, 89385 (1977)

    Google Scholar 

  118. Gross, D. E.: USP 3989761; C. A. 86, 72193 (1977)

    Google Scholar 

  119. Fishel, N. A., Gross, D. E.: USP 4035428; C. A. 87, 134 589 (1977)

    Google Scholar 

  120. Fishel, N. A., Anvil, S. R., Gross, D. E.: Catalog Org. Synth. 1978, 119 (7th ed.)

    Google Scholar 

  121. Müller, K. W.: USP 2862035; C. A. 53, 9157 (1959)

    Google Scholar 

  122. Kagaku, S.: Jap. P. 81,20533, C. A. 95, 42640 91981)

    Google Scholar 

  123. La Count, R. B., Friedman, S.: J. Org. Chem. 42, 2751 (1977)

    Google Scholar 

  124. 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. Bunnett, J. F., Zahler, R. E.: Chem. Rev. 49, 273 (1951)

    Google Scholar 

  126. Davies, D. I., Hey, D. H., Williams, G. H.: J. Chem. Soc. (London) 1961, 562

    Google Scholar 

  127. Hawthorne, M. F.: J. Org. Chem. 22, 1001 (1957)

    Google Scholar 

  128. Kuivila, H. G.: J. Am. Chem. Soc. 76, 870 (1954)

    Google Scholar 

  129. Yarboro, T. L., Karr, C.: J. Org. Chem. 24, 1141 (1959)

    Google Scholar 

  130. Eberson, L., Jönsson, L., Wistrand, L.-G.: Tetrahedron 38, 1087 (1982) and lit. cit. therein

    Google Scholar 

  131. Eberhardt, M. K.: J. Org. Chem. 42, 832 (1977); J. Phys. Chem. 81, 1051 (1977)

    Google Scholar 

  132. Zoratti, M., Bunnett, J. M.: J. Org. Chem. 45, 1769 (1980)

    Google Scholar 

  133. Bunnett, J. F.: Acc. Chem. Res. 11, 413 (1978)

    Google Scholar 

  134. Kornblum, N.: Angew. Chem. 87, 797 (1975); Angew. Chem. engl. 14, 734 (1975)

    Google Scholar 

  135. Russell, G. A., Danen, W. C.: J. Am. Chem. Soc. 90, 347 (1968) and later publications

    Google Scholar 

  136. Cerfontain, H.: J. Org. Chem. 47, 4680 (1982)

    Google Scholar 

  137. Suzumura, H.: Bl. chem. Soc. Japan 35, 108 (1962)

    Google Scholar 

  138. Hay, A. S., Clark, R. F.: Makromolecules 3, 533 (1970)

    Google Scholar 

  139. Hay, A. S.: Fr. P. 1521 799; C. A. 71, 61006 (1969)

    Google Scholar 

  140. Plešek, J.: Chem. Listy 50, 246 (1956); C.A. 50, 7732 (1956) Coll. Czech. Chem. Commun. 21, 275 (1956)

    Google Scholar 

  141. Munk, P., Plešek, J.: Chem. Listy 51, 771 (1957); C.A. 51, 11261 (1957)

    Google Scholar 

  142. Plešek, J., Munk, P.: ibid. 51, 633 (1957)

    Google Scholar 

  143. Munk, P., Plešek, J.: ibid 51, 771 (1957); C.A. 51, 11261 (1957)

    Google Scholar 

  144. see also Kunze, H.: Ber. dtsch. Chem. Ges. 59, 2085 (1926)

    Google Scholar 

  145. de Jonge, C. R. H. I., van Dort, H. M., Vollbracht, L.: Tetrahedron Lett. 1970, 1881

    Google Scholar 

  146. Hay, A. S.: Brit. P. 1207524 (1967); C.A. 77, 126220 (1967)

    Google Scholar 

  147. Kapner, R. S., Kippax, D. L., Murphy, K. E., Udani, H. H.: Germ. P. 163402; C.A. 83, 163813 (1975)

    Google Scholar 

  148. see also Brit. P. 1207524; C.A. 77, 126220 (1972)

    Google Scholar 

  149. Hay, A. S.: see lit. 61; Boon, J., Mayer, E. P.: J. Polymer Sci. 7, 205 (1969)

    Google Scholar 

  150. Schwarz, H. H., Metten, J., Koeller, H. Tacke, P., Weissel, O.: Germ. Offen 2.102746 (1971); C.A. 77 126218 (1972)

    Google Scholar 

  151. Naarman, H., Brandstetter, F., Schuster, H. H.: Europ. Appl. P. EP 47824; C.A. 96, 218455, 218418 (1982)

    Google Scholar 

  152. Hay, A. S., Blanchard, H. S., Endres, G. F., Eustance, J. W.: J. Am. Chem. Soc. 81, 6335 (1959)

    Google Scholar 

  153. see also Hay, A. S.: J. Org. Chem. 27, 3320 (1962); the Cu(I) complex is also very valuable for oxidative acetylene coupling

    Google Scholar 

  154. Hay, A. S.: Tetrahedron Lett. 1965, 4241

    Google Scholar 

  155. Winnacker-Küchler: Chemische Technologie, 4. ed., vol. 6, Carl Hanser Verlag, München 1982

    Google Scholar 

  156. Hay, A. S.: Advances Polymer Sci. 58, 581 (1962)

    Google Scholar 

  157. Endres, G. F., Hay, A. S., Eustance, J. W.: J. Org. Chem. 28, 1300 (1963)

    Google Scholar 

  158. 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. Davies, G., El Sayed, M. A., Fasano, R. E.: Inorg. Chim. Acta 71, 95 (1983) and lit. cited therein

    Google Scholar 

  160. Capdevielle, P., Maumy, M.: Tetrahedron Lett. 24, 5611 (1983)

    Google Scholar 

  161. King, F. D., Walton, D. R. M.: Synthesis 1976, 40

    Google Scholar 

  162. Pinhey, J. T., Rowe, B. A.: Aust. J. Chem. 33, 113 (1980)

    Google Scholar 

  163. 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. 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, 930

    Google Scholar 

  165. LiCuPh2 and p-tolyazocyclohexene: Sacks, C. E., Fuchs, P. L.: J. Am. Chem. Chem. Soc. 97, 7372 (1975)

    Google Scholar 

  166. McKillop, A., Rao, D. P.: Syntheses 1977, 759

    Google Scholar 

  167. Krapcho, A. P., Lovey, A. J.: Tetrahedron Lett. 1973, 957

    Google Scholar 

  168. Barton, D. H. R., Papoula, H. T. B., Guilhem, J., Motherwell, W. B., Pascard, C., Huu Dau, E.: J. Chem, Soc. Chem. Commun. 1982, 732

    Google Scholar 

  169. Barton, D. H. R., Lester, D. J. L., Motherwell, W., Papoula, M. T.: ibid. 1980, 246

    Google Scholar 

  170. Pinhey, J. T., Rowe, B. A.: Aust. J. Chem. 36, 789 (1983)

    Google Scholar 

  171. Horning, E. C., Horning, M. C.: J. Am. Chem. Soc. 69, 1359 (1947)

    Google Scholar 

  172. Woods, G. F., Tucker, I. W.: ibid 70, 2174 (1948)

    Google Scholar 

  173. Review: Posner, G. H.: Organic Reactions 19, 1 (1972)

    Google Scholar 

  174. Malmberg, H., Nilsson, M., Ullenius, C.: Tetrahedron Lett. 23, 3823 (1982); Review: Normant, J. F.: Synthesis 1972, 63

    Google Scholar 

  175. Woods, G. F., Reed, F. T., Arthur, T. E., Ezekiel, H.: J. Am. Chem. Soc. 73, 3854 (1951)

    Google Scholar 

  176. Petrow, A. D.: Ber. dtsch. Chem. Ges. 62, 642 (1929) and cited lit.; ibid. 63, 898 (1930)

    Google Scholar 

  177. Kenner, J., Shaw, H.: J. Chem. Soc. (London) 1931, 769

    Google Scholar 

  178. Sexsmith, D. R., Rassweiler, J. H.: J. Org. Chem. 25, 1229 (1960); see also lit. 99)

    Google Scholar 

  179. 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, 1451

    Google Scholar 

  180. Egli, C., Helali, S. E., Hardegger, E.: Helv. Chim. Acta 58, 104 (1975)

    Google Scholar 

  181. Zimmerman, H. E., Schuster, D. I.: J. Am. Chem. Soc. 84, 4527 (1962)

    Google Scholar 

  182. 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, 3926

    Google Scholar 

  183. 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. Yates, P., Hyre, J. E.: J. Org. Chem. 27, 4101 (1962)

    Google Scholar 

  185. 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. Eicher, T., v. Angerer F. Lichigs Ann. 746, 120 (1971)

    Google Scholar 

  187. Ried, W., König, E.: ibid. 757, 153 (1972)

    Google Scholar 

  188. see also Perst, H., Wesemeyer, I.: Tetrahedron Lett. 1970, 4189

    Google Scholar 

  189. Suter, C. M., Smith, P. G.: J. Am. Chem. Soc. 61, 166 (1939)

    Google Scholar 

  190. Ames, G. R., Davey, W.: J. Chem. Soc. London, 1957, 3480, 1958, 1794

    Google Scholar 

  191. Betts, B. E., Davey, W.: ibid, 1961, 1683, 3440

    Google Scholar 

  192. see also Fichter, F., Grether, E.: Ber. dtsch. Chem. Ges. 36, 1407 (1903)

    Google Scholar 

  193. Harrison Jr., E. A.: J. Org. Chem. 44, 1807 (1979)

    Google Scholar 

  194. Ueji, S., Nakatsu, K., Yoshioka, H., Kinoshita, K.: Tetrahedron Lett. 1982, 1173

    Google Scholar 

  195. Jones, E. C. S., Kenner, J.: J. chem. Soc. (London) 1931, 769; 1842

    Google Scholar 

  196. Hay, A. S.: J. Org. Chem. 30, 3577 (1965)

    Google Scholar 

  197. Bordwell, F. G., Wellmann, K. M.: ibid. 29, 509 (1964)

    Google Scholar 

  198. Worschech, K.: Dissertation Univ. Marburg 1960; see also lit. 137)

    Google Scholar 

  199. Kvalnes, D. E.: J. Am. Chem. Soc. 56, 2478 (1934)

    Google Scholar 

  200. Zimmerman, H. E.: Angew. Chem. 81, 45 (1969); engl. 8, 1

    Google Scholar 

  201. Zimmerman, H. E., Epling, G. A.: J. Am. Chem. Soc. 94, 7806 (1972)

    Google Scholar 

  202. Dannenberg, W., Lemmer, D., Perst, H.: Tetrahedron Lett. 1974, 2133

    Google Scholar 

  203. Dannenberg, W.: Dissertation Univ. Marburg 1975

    Google Scholar 

  204. Rau, W.: Dipl. Arb. Univ. Marburg 1980

    Google Scholar 

  205. the mechanism of these and similar rearrangements has been fully studied by Perst and coworkers, see e.g. Perst, H.: Habil. Arbeit, Univ. Marburg 1972

    Google Scholar 

  206. Dannenberg, W., Perst, H.: Liebigs Ann. Chem. 1975, 1873

    Google Scholar 

  207. Dannenberg, W., Perst, H., Seifert, W. J.: Tetrahedron Lett. 1975, 3481

    Google Scholar 

  208. Weisskopf, V., Perst, H.: Liebigs Ann. 1978, 1634

    Google Scholar 

  209. Monahan, A. S.: J. Org. Chem. 33, 1441 (1968)

    Google Scholar 

  210. Eistert, B., Langbein, A.: Liebigs Ann. Chem. 678, 78 (1964)

    Google Scholar 

  211. Eistert, B., Thommen, A. J.: Chem. Ber. 104, 3048 (1971)

    Google Scholar 

  212. Dürr, H., Heilkämper, P.: Liebigs Ann. Chem. 716, 212 (1968)

    Google Scholar 

  213. Hart, H. Raggon, J. W.: Tetrahedron Lett. 24, 4891 (1983)

    Google Scholar 

  214. Evans, D. A., Hoffmann, J. M., Truesdale, L. K.: J. Am. Chem. Soc. 95, 5822 (1973)

    Google Scholar 

  215. Evans, D. A., Hart, D. J., Koelsch, P. M., Chain, P. A.: Pure and Appl. Chem. 51, 1285 (1979) and lit. cit. therein

    Google Scholar 

  216. see also Parker, K. A., Kang, S.-K.: J. Org. Chem. 45, 1218 (1980)

    Google Scholar 

  217. Liotta, D., Saindane, M., Barnum, C.: J. Org. Chem. 46, 3369 (1981)

    Google Scholar 

  218. Fischer, A., Henderson, G. N.: Tetrahedron Lett. 24, 131 (1983) and lit. cit. therein

    Google Scholar 

  219. Rieker, A., Hernes, G.: Tetrahedron Lett. 1968, 3775

    Google Scholar 

  220. Rieker, A.: Angew. Chem. 81, 938 (1969); engl. 8, 918 (1969)

    Google Scholar 

  221. Dimroth, K., Berndt, A., Volland, R.: Chem. Ber. 99, 3040 (1966)

    Google Scholar 

  222. Berndt, A.: Dissertation Univ. Marburg 1965

    Google Scholar 

  223. Dimroth, K., Vogel, K., Krafft, W.: Chem. Ber. 101, 2215 (1968)

    Google Scholar 

  224. Michel, W.: Dissertation Univ. Marburg 1961

    Google Scholar 

  225. Müller, E., Schick, A., Scheffler, K.: Chem. Ber. 92, 474 (1959)

    Google Scholar 

  226. Müller, E., Schick, A., Mayer, R., Scheffler, K.: ibid. 93, 2649 (1960)

    Google Scholar 

  227. Dimroth, K., Berndt, A., Reichardt, C.: Organic Synthesis, Coll. Vol. 5, 1128 (1973)

    Google Scholar 

  228. Dimroth, K., Berndt, A., Perst, H., Reichardt, C.: ibid. p. 1130

    Google Scholar 

  229. Dimroth, K., Reichardt, C., Vogel, K.: ibid. p. 1135

    Google Scholar 

  230. Blöcher, K. H.: Dissertation Univ. Marburg 1961

    Google Scholar 

  231. Dimroth, K., Kalk, F. Sell, R., Schlömer, K.: Liebigs Ann. Chem. 624, 51 (1959)

    Google Scholar 

  232. Dimroth, K., Wolf, K. H.: Angew. Chem. 72, 777 (1960)

    Google Scholar 

  233. 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. Lendenfeld, H.: Monatsh. 27, 969 (1906); Ariyan, Z. S., Mooney, B.: J. Chem. Soc. (London) 1962, 1519

    Google Scholar 

  235. Wache, H.: Dissertation Univ. Marburg 1964

    Google Scholar 

  236. Dimroth, K., Wache, H.: Chem. Ber. 99, 399 (1966)

    Google Scholar 

  237. Laubert, G.: Dissertation Univ. Marburg 1968

    Google Scholar 

  238. Dimroth, K., Laubert, G., Blöcher, K. H.: Liebigs Ann. Chem. 765, 133 (1972)

    Google Scholar 

  239. Güsten, H., Kirsch, G., Schulte-Frohlinde, D.: Angew. Chem. 79, 941 (1967); engl. 6, 948 (1967); Tetrahedron 24, 4393 (1968)

    Google Scholar 

  240. Dimroth, K., Schromm, K.: unpublished results 1962

    Google Scholar 

  241. 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. Griller, D., Barclay, L. R., Ingold, K. U.: J. Am. Chem. Soc. 97, 6151 (1975) and lit. cited therein

    Google Scholar 

  243. see also Chattaway, F. D., Orton, K. J. P.: J. Chem. Soc. (London) 79, 461 (1901)

    Google Scholar 

  244. Goldschmidt, St.: Ber. dtsch. chem. Ges. 46, 2728 (1913)

    Google Scholar 

  245. see also Hedayatullah, M., Denivelle, L.: Compt. Rend. Acad. Sci. Paris 258, 5467 (1964); 259, 5516 (1965); Bull. Soc. Chim. France 1969, 4168

    Google Scholar 

  246. see also Schultz, G.: Ber. dtsch. chem. Ges. 17, 461 (1884)

    Google Scholar 

  247. Oosterloo, G.: Dissertation Univ. Marburg 1958

    Google Scholar 

  248. Dimroth, K., Oosterloo, G.: Angew. Chem. 70, 165 (1958)

    Google Scholar 

  249. 2.4.6-Triphenylselenophenol see Kataeva, L. M., Kataev, E. T.: Zh. obć 32, 2712 (1962)

    Google Scholar 

  250. Dimroth, K., Kraft, K. J.: Angew. Chem. 76, 433 (1964); engl. 3, 384 (1964)

    Google Scholar 

  251. Kraft, K. J.: unpublished results, Univ. Marburg 1965

    Google Scholar 

  252. 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. Bordwell, G. F., Mc Callum, R. J., Olmstead, W. N.: J. Org. Chem. 49, 1424 (1984)

    Google Scholar 

  254. Nakano, F., Sugishita, M.: Jap. P 74 40227; C.A. 82, 155 777 (1975).

    Google Scholar 

  255. 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. King, I. R., Hildon, A. M.: USP 4002693; C.A. 86, 120975 (1977)

    Google Scholar 

  257. Raychaudhuri, S. R.: Chem. and Ind. (London) 1980, 293

    Google Scholar 

  258. Kawamoto, A., Uda, H., Harada, N.: Bull. Chem. Soc. Japan 53, 3279 (1980)

    Google Scholar 

  259. Hay, A.: USP 3363008; C.A. 69, 2702 (1968)

    Google Scholar 

  260. Masamune, S., Casellucci, N. T.: J. Chem. Soc. (London), Proc. 1964, 298

    Google Scholar 

  261. Dürr, H.: Tetrahedron Lett. 1966, 5829; Liebigs Ann. Chem. 711, 115 (1968)

    Google Scholar 

  262. Farnum, D. G., Burr, M.: J. Am. Chem. Soc. 82, 2651 (1951)

    Google Scholar 

  263. Dana, D. E., Hay, A. S.: Synthesis 1982, 164: Improved synthesis and 4′, 4″ substituted derivatives, see also cited literature

    Google Scholar 

  264. 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, CH2CO2H

    Google Scholar 

  265. Dimroth, K., Kaletsch, H.: unpubl. 1982 from (1) + CH2O and NaOH in EtOH

    Google Scholar 

  266. De Jonge, C. R. H., Hageman, H. J., Huysmans, W. B. G., Hijs, W. J.: J. Chem. Soc. (London), Perkin II, 1973, 1276

    Google Scholar 

  267. Stillson, G. H., Sawyer, D. W., Hunt, C. K.: J. Am. Chem. Soc. 67, 303 (1945)

    Google Scholar 

  268. Müller, E., Schick, A., Scheffler, K.: Chem. Ber. 92, 474 (1959)

    Google Scholar 

  269. Müller, E., Schick, A., Mayer, R., Scheffler, K.: Chem. Ber. 93, 2649 (1960)

    Google Scholar 

  270. Hammel, D. E.: Dissertation Univ. Marburg 1964

    Google Scholar 

  271. Dimroth, K., Tüncher, W., Kaletsch, H.: Chem. Ber. 111, 264 (1978)

    Google Scholar 

  272. Tüncher, W.: Dissertation Univ. Marburg 1976

    Google Scholar 

  273. 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. Umbach, W.: Dissertation Univ. Marburg 1962

    Google Scholar 

  275. Umbach, W., Dimroth, K.: 1963 not published

    Google Scholar 

  276. Müller, K. H.: Dissertation Univ. Marburg 1963

    Google Scholar 

  277. El-Kholy, I., Mishrikey, M. M., Rafla, F. K., Soliman, G.: J. Chem. Soc. (London), 1962 5153

    Google Scholar 

  278. Ried, W., Kunkel, W., Strätz, A.: Liebigs Ann. Chem. 726, 69 (1969)

    Google Scholar 

  279. Musso, H., v. Grunelius, S.: Chem. Ber. 92, 3101 (1959)

    Google Scholar 

  280. Barker, A. W., Kerlinger H, O., Shulgin, A. T.: Spectrochim. Acta 20, 1477 (1964)

    Google Scholar 

  281. Goddu, R. F.: J. Am. Chem. Soc. 82, 4533 (1960)

    Google Scholar 

  282. Ingold, K. U., Taylor, D. R.: Can. J. Chem. 39, 471 (1961)

    Google Scholar 

  283. Hay, A. S., Boulette, B. M.: J. Org. Chem. 41, 1710 (1976)

    Google Scholar 

  284. Waters, W. A.: J. Chem. Soc. (London) B 1971, 2026

    Google Scholar 

  285. Allmann, R., Hellner, E.: Chem. Ber. 101, 2522 (1968)

    Google Scholar 

  286. For discussion see Rieker, A. in Houben-Weyl vol. VII 3b, part 2, p. 523 (1979)

    Google Scholar 

  287. Land, E. J., Porter, G., Strachan, E.: Trans. Faraday Soc. 57, 1885 (1961); 59, 2016 (1963)

    Google Scholar 

  288. 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, 1237

    Google Scholar 

  289. Burlatsky, S. F., Levin, P. P., Khudjakov, I. V., Kuzmin, V. A., Ovchinnikov, A. A.: Chem. Phys. Lett. 66, 565 (1979)

    Google Scholar 

  290. for pulse radiolysis see also Neta, P.: J. Chem. Ed. 58, 110 (1981) for a short review

    Google Scholar 

  291. Ziegler, K., Ewald, L.: Liebigs Ann. Chem. 473, 163 (1929)

    Google Scholar 

  292. Dimroth, K., Berndt, A., Bär, F., Schweig, A., Volland, R.: Angew. Chem. 79, 69 (1967); engl. 6, 34 (1967)

    Google Scholar 

  293. Hyde, J. S.: J. Phys. Chem. 71, 68 (1967)

    Google Scholar 

  294. Cook, C. D., Depatie, C. B., English, E. S.: J. Org. Chem. 24, 1356 (1959)

    Google Scholar 

  295. Dimroth, K., Kraft, K. J.: Chem. Ber. 99, 264 (1966)

    Google Scholar 

  296. Kraft, K. J.: Dissertation Univ. Marburg 1963

    Google Scholar 

  297. Braude, E. A., Brook, A. G., Linstead, R. P.: J. Chem. Soc. (London) 1954, 3569

    Google Scholar 

  298. Part 13: Braude, E. A., Jackman, L. M., Linstead, R. P., Lowe, G.: ibid. 1960, 3133

    Google Scholar 

  299. Reviews: Walker, D., Hiebert, J. H.: Chem. Rev. 67, 153 (1967)

    Google Scholar 

  300. Jackman, L. M.: Adv. Organic Chem. vol. 2, 329 (1960); Interscience, New York.

    Google Scholar 

  301. 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, 4540

    Google Scholar 

  302. Nickel, B., Mauser, H., Hezel, U.: Z. Phys. Chem. N.F. 54, 196, 214 (1967)

    Google Scholar 

  303. Mauser, H., Nickel, B.: Angew. Chem. 77, 378 (1965); engl. 4, 354 (1965).

    Google Scholar 

  304. Steenken, S.; Neta, P.: J. Phys. Chem. 86, 3661 (1982)

    Google Scholar 

  305. Gasanov, B. R., Stradyn', Y. P.: J. Gen. Chem. of USSR, engl. 46, 2469 (1976)

    Google Scholar 

  306. Müller, E., Rieker, A., Schick, A.: Liebigs Ann. Chem. 673, 40 (1964)

    Google Scholar 

  307. Rieker, A.: Chem. Ber. 98, 715 (1965)

    Google Scholar 

  308. Becker, H.-D.: J. Org. Chem. 29, 3068 (1964); 30, 982 (1965)

    Google Scholar 

  309. Dimroth, K., Berndt, H.: Chem. Ber. 101, 2519 (1968)

    Google Scholar 

  310. Dimroth, K., Tüncher, W.: Synthesis 1977, 339

    Google Scholar 

  311. Haaß, K.: Dissertation Univ. Marburg 1962

    Google Scholar 

  312. Criegée, R.: Ber. dtsch. Chem. Ges. 69, 2758 (1936)

    Google Scholar 

  313. Reviews: Zollinger, H.: Angew. Chem. 70, 204 (1958)

    Google Scholar 

  314. Krumbiegl, P.: Isotopieeffekte, Akademie Verlag, Berlin 1970

    Google Scholar 

  315. Hageman, H. J., Huysmans, W. G. B.: J. Chem. Soc. Chem. Commun. 1969, 837.

    Google Scholar 

  316. For similar reactions by heating 2,6,2′,6′-tetraphenyldiphenoquinone see Hay, A. S.: J. Org. Chem. 36, 218 (1971)

    Google Scholar 

  317. 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. Reviews: Rotermund, G. W.: Houben Weyl IV 1b, 761 (1975)

    Google Scholar 

  319. Wedemeyer, K. F.: ibid. VI 1c, (1976)

    Google Scholar 

  320. Ulrich, H., Richter, R.: ibid, VII 3a, 27 (1977)

    Google Scholar 

  321. Boldt, P.: ibid. VII 3a, 27 (1977)

    Google Scholar 

  322. Barton, D. H. R.: Chem. in Britain 3, 330 (1967) and lit. cit. therein

    Google Scholar 

  323. Musso, H.: Angew. Chem. 75, 965 (1963)

    Google Scholar 

  324. see also Bird, C. W., Chauhan, Y.-P.: Tetrahedron Lett. 1978, 2133

    Google Scholar 

  325. Teuber, H. J., Glossauer, G.: Chem. Ber. 98, 2643 (1965)

    Google Scholar 

  326. 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 solvents

    Google Scholar 

  327. Finkbeiner, H., Toothacker, A. T.: J. Org. Chem. 33, 4347 (1965)

    Google Scholar 

  328. Dewar, M. J. S., Nakaya, T.: J. Am. Chem. Soc. 90, 7134 (1968)

    Google Scholar 

  329. Vogt Jr., L. H., Wirth, J. G., Finkbeiner, H. L.: J. Org. Chem. 34, 273 (1969)

    Google Scholar 

  330. Bolton, D. A.: ibid. 34, 2031 (1969)

    Google Scholar 

  331. 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 therein

    Google Scholar 

  332. Martius, C., Eilingsfeld, H.: Liebigs Ann. Chem. 607, 159 (1957)

    Google Scholar 

  333. Adler, E., Falkehag, I., Smith, B.: Acta Chim. Scand. 16, 529 (1962)

    Google Scholar 

  334. Suttie, A. B.: Tetrahedron Lett. 1969, 953

    Google Scholar 

  335. Rolán, A., Parker, V. D.: J. Chem. Soc. (London) (C) 1971, 3214

    Google Scholar 

  336. Rolán, A.: J. Chem. Soc., Chem. Commun. 1971, 1643

    Google Scholar 

  337. Nilsson, A., Palmquist, U., Pettersson, T., Rolán, A.: (part 5), J. Chem. Soc. (London), Perkin I, 1978, 696 and lit. cit. therein

    Google Scholar 

  338. Rieker, A., Dreher, E.-L., Geisel, H., Khalifa, M. H.: Syntheses 1978, 851

    Google Scholar 

  339. Speiser, B., Rieker, A.: J. Elektrol. Chem. 110, 231 (1980)

    Google Scholar 

  340. Review: Evans, D. H.: Acc. Chem. Res. 10, 313 (1977)

    Google Scholar 

  341. Rieker, A., Bracht, J., Dreher, E. L., Schneider, P.: Houben-Weyl, vol. VII 3b, 529 (1979)

    Google Scholar 

  342. Dimroth, K., Umbach, W., Thomas, H.: Chem. Ber. 100, 132 (1967), see also ref. 166)

    Google Scholar 

  343. Dimroth, K., Thomas, H.: Chem. Ber. 102, 3795 (1969)

    Google Scholar 

  344. Thomas, H.: Dissertation Univ. Marburg 1968

    Google Scholar 

  345. 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. 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. Wessely, F., Sinwel, F.: Monatsh. Chem. 81, 1055 (1950)

    Google Scholar 

  348. Dimroth, K., Perst, H., Schlömer, K., Worschech, K., Müller, K.-H.: Chem. Ber. 100, 629 (1967)

    Google Scholar 

  349. Rieker, A., Rundel, W., Kessler, H.: Z. Natforsch. 24b, 547 (1969)

    Google Scholar 

  350. Sell, R.: Dissertation Universität Marburg 1960; see also ref. 133)

    Google Scholar 

  351. Dimroth, K., Perst, H.: Liebigs Ann. Chem. 708, 86 (1967), see also Perst, H.: Dissertation Universität Marburg 1965

    Google Scholar 

  352. Dimroth, K., Perst, H., Müller, K.-H.: Chem. Ber. 100, 1850 (1967); see also ref. 168)

    Google Scholar 

  353. Zbiral, E., Wessely, F., Lahrmann, L.: Monatsh. Chem. 91, 92 (1960)

    Google Scholar 

  354. Nishinaga, A., Itahara, T., Matsuura, T., Berger, S., Henes, G., Rieker, A.: Chem. Ber. 109, 1530 (1976)

    Google Scholar 

  355. Perst, H., Dimroth, K.: Tetrahedron 24, 5385 (1968)

    Google Scholar 

  356. Perst, H., Sprenger, W.: Tetrahedron Lett. 1970, 3601

    Google Scholar 

  357. Perst, H., Wesemeier, I.: ibid. 1970, 4189

    Google Scholar 

  358. Lemmer, D., Perst, H.: ibid. 1972, 2735

    Google Scholar 

  359. Seifert, W. J., Perst, H., Dannenberg, W.: ibid. 1973, 4999

    Google Scholar 

  360. Seifert, W., Perst H.: ibid. 1975, 2419

    Google Scholar 

  361. Dannenberg, W., Seifert, W. J., Perst, H.: ibid. 1975, 3481

    Google Scholar 

  362. Perst, H., Dannenberg, W.: Liebigs Ann. Chem. 1975, 1873

    Google Scholar 

  363. Weisskopf, V., Perst, H.: Liebigs Ann. Chem. 1978, 1634

    Google Scholar 

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Dimroth, K. (1985). Arylated phenols, aroxyl radicals and aryloxenium ions syntheses and properties. In: Photochemistry and Organic Synthesis. Topics in Current Chemistry, vol 129. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-15141-9_3

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