Advertisement

Carbohelicenes and heterohelicenes

  • Wim H. Laarhoven
  • Wim J. C. Prinsen
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 125)

Keywords

High Performance Liquid Chromatography Benzene Ring Asymmetric Synthesis Optical Yield Cholesteric Liquid Crystal 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

11 References

  1. 1.
    Newman, M. S., Lednicer, D.: J. Am. Chem. Soc. 78, 4765 (1956)CrossRefGoogle Scholar
  2. 2.
    Hugelshofer, P., Kalvoda, J., Schaffner, K.: Helv. Chim. Acta 43, 1322 (1960)CrossRefGoogle Scholar
  3. 3.
    Flammang-Barbieux, M., Nasielski, J., Martin, R. H.: Tetrahedron Lett. 743 (1967)Google Scholar
  4. 4.
    Wijnberg, H., Groen, M. B.: J. Am. Chem. Soc. 90, 5339 (1968)CrossRefGoogle Scholar
  5. 5.
    Wijnberg, H.: Accounts Chem. Res. 4, 65 (1971)CrossRefGoogle Scholar
  6. 6.
    Martin, R. H.: Angew. Chem. Int. Ed. 13, 649 (1974)CrossRefGoogle Scholar
  7. 7.
    Laarhoven, W. H.: Recl. Trav. Chim. (Pays-Bas) 102, 185 (1983)Google Scholar
  8. 8.
    Mallory, F. B., Mallory, C. W. in: Org. Reactions, J. Wiley & Sons, New York 1984, Vol. 30, p. 1Google Scholar
  9. 9.
    Maercken, A., in: Org. Reactions, J. Wiley & Sons, New York 1965, Vol. 14, p. 270Google Scholar
  10. 10.
    Siegrist, A. E., Meijer, H. R.: Helv. Chim. Acta 52, 1282, 2521 (1969)CrossRefGoogle Scholar
  11. 11.
    Jutz, C., Loebering, H. G.: Angew. Chem. 87, 415 (1975)Google Scholar
  12. 12.
    Muszkat, K. A.: Topics Curr. Chem. 88, 89 (1980)Google Scholar
  13. 13.
    Scholz, M., Mühlstadt, M., Dietz, F.: Tetrahedron Lett. 665 (1967)Google Scholar
  14. 14. a)
    Laarhoven, W. H., Cuppen, J. H. M., Nivard, R. J. F.: Recl. Trav. Chim. (Pays-Bas) 87, 687 (1968)Google Scholar
  15. 14. b)
    Laarhoven, W. H., Cuppen, Th. J. H. M., Nivard, R. J. F.: Tetrahedron 26, 4865 (1970)CrossRefGoogle Scholar
  16. 15. a)
    Wismonski-Knittel, T., Fischer, E.: Mol. Photochem. 9, 67 (1978)Google Scholar
  17. 15. b)
    Wismonski-Knittel, T., Fischer, E.: J. Chem. Soc. Perkin II, 1979, 449Google Scholar
  18. 16.
    Laarhoven, W. H., Cuppen, Th. J. H. M., Brinkhof, H. H. K.: Tetrahedron 38, 3179 (1982)CrossRefGoogle Scholar
  19. 17. a)
    Grellmann, K. H., Hentzschel, P., Wismonski-Knittel, T., Fischer, E.: J. Photochem. 11, 197 (1979)CrossRefGoogle Scholar
  20. 17. b)
    Tinnemans, A. H., Laarhoven, W. H., Sharafi-Ozeri, S., Muszkat, K. A.: Recl. Trav. Chim. (Pays-Bas) 94, 239 (1975)Google Scholar
  21. 18.
    Tinnemans, A. H. A., Laarhoven, W. H.: J. Am. Chem. Soc. 96, 4611 (1974)CrossRefGoogle Scholar
  22. 19.
    Laarhoven, W. H., Boumans, P. G. F.: Recl. Trav. Chim. (Pays-Bas) 94, 114 (1975)Google Scholar
  23. 20.
    Joly, M., Defay, N., Martin, R. H., Declerq, J. P., Germain, G., Soubrier-Payen, B., van Meerssche, M.: Helv. Chim. Acta 60, 537 (1977)CrossRefGoogle Scholar
  24. 21.
    Laarhoven, W. H., Cuppen, Th. J. H. M.: Tetrahedron 30, 1101 (1974)CrossRefGoogle Scholar
  25. 22.
    Somers, J. B. M.: Thesis, Nijmegen 1984Google Scholar
  26. 23.
    Laarhoven, W. H., Veldhuis, R. G. M.: Tetrahedron 28, 1811 (1972)CrossRefGoogle Scholar
  27. 24.
    Gorsane, M.: Thesis, Brussels 1977Google Scholar
  28. 25.
    Laarhoven, W. H., Veldhuis, R. G. M.: Tetrahedron 28, 1823 (1972)CrossRefGoogle Scholar
  29. 26.
    Vanest, J. M., Gorsane, M., Libert, V., Pecher, J., Martin, R. H.: Chimia 29, 343 (1975)Google Scholar
  30. 27.
    Laarhoven, W. H., Cuppen, Th. J. H. M., Nivard, R. J. F.: Tetrahedron 26, 4865 (1970)CrossRefGoogle Scholar
  31. 28.
    Martin, R. H., Marchant, M. J., Baes, M.: Helv. Chim. Acta 54, 358 (1971)CrossRefGoogle Scholar
  32. 29.
    Martin, R. H., Flammang-Barbieux, M., Cosyn, J. P., Gelbcker, M.: Tetrahedron Lett. 3507 (1968)Google Scholar
  33. 30.
    Martin, R. H., Cosyn, J. P.: Synth. Comm. 1, 257 (1971)Google Scholar
  34. 31.
    R. H. Martin, Libert, V.: J. Chem. Res. (s) 130 (1980)Google Scholar
  35. 32.
    Martin, R. H., Baes, M.: Tetrahedron 31, 2135 (1975)CrossRefGoogle Scholar
  36. 33.
    Martin, R. H., Morren, G., Schurter, J. J.: Tetrahedron Lett. 3863 (1969)Google Scholar
  37. 34.
    Laarhoven, W. H., Nivard, R. J. F.: Tetrahedron 32, 2445 (1976)CrossRefGoogle Scholar
  38. 35.
    Laarhoven, W. H., Cuppen, Th. J. H. M.: Tetrahedron Lett. 163 (1971)Google Scholar
  39. 36.
    Martin, R. H., Eijndels, Ch., Defay, N.: ibid. 2731 (1972)Google Scholar
  40. 37.
    Laarhoven, W. H., Cuppen, Th. J. H. M.: Recl. Trav. Chim. (Pays-Bas) 92, 553 (1973)Google Scholar
  41. 38.
    Laarhoven, W. H., de Jong, M. H.: ibid. 92, 651 (1973)Google Scholar
  42. 39.
    Martin, R. H., Eijndels, Ch., Defay, N.: Tetrahedron 30, 3339 (1974)CrossRefGoogle Scholar
  43. 40.
    Laarhoven, W. H., Cuppen, Th. J. H. M., Nivard, R. J. F.: ibid. 30, 3343 (1974)CrossRefGoogle Scholar
  44. 41.
    Borkent, J. H., Diesveld, J. W., Laarhoven, W. H.: Recl. Trav. Chim. (Pays-Bas) 100, 114 (1981)Google Scholar
  45. 42.
    Imajo, S., Shingu, K., Kuritani, H., Kato, A.: Tetrahedron Lett. 22, 107 (1981)CrossRefGoogle Scholar
  46. 43.
    Borkent, J. H., Diesveld, J. W., Laarhoven, W. H.: Tetrahedron 38, 1809 (1982)CrossRefGoogle Scholar
  47. 44. a)
    Tinnemans, A. H. A., Laarhoven, W. H.: J. Chem. Soc. Perkin II 1111, 1115 (1976)Google Scholar
  48. 44. b)
    Tinnemans, A. H. A., Laarhoven, W. H.: Org. Photochem. Synth. Vol. 2, p. 93 (1976)Google Scholar
  49. 45.
    Laarhoven, W. H., Peters, W. H. M., Tinnemans, A. H. A.: Tetrahedron 34, 769 (1978)CrossRefGoogle Scholar
  50. 46.
    Tinnemans, A. H. A., Laarhoven, W. H.: ibid. 35, 1537 (1979)CrossRefGoogle Scholar
  51. 47.
    Voegtle, F., Atzmueller, M., Wehner, W., Gruetze, J.: Angew. Chem. 89, 338 (1977)Google Scholar
  52. 48.
    Mislow, K., Gust, D., Finocchiaro, P., Boettcher, R. J.: Top. Curr. Chem. 47, 1 (1974)Google Scholar
  53. 49.
    Voegtle, F., Höhner, G.: Angew. Chem. 87, 522 (1975)Google Scholar
  54. 50.
    Thulin, B., Wennerstrom, O.: Acta Chem. Scand. B30, 688 (1976)Google Scholar
  55. 51.
    Mulliken, R. S.: J. Chem. Phys. 23, 1833, 1841 (1955)CrossRefGoogle Scholar
  56. 52. a)
    Muszkat, K. A., Sharafi-Ozeri, S.: Chem. Phys. Lett. 20, 397 (1973)CrossRefGoogle Scholar
  57. 52. b)
    Muszkat, K. A., Seger, G., Sharafi-Ozeri, S.: J. C. S. Faraday II 71, 1529 (1975)CrossRefGoogle Scholar
  58. 53.
    Dopper, J. H., Oudman, D., Wijnberg, H.: J. Am. Chem. Soc. 95, 3692 (1973)CrossRefGoogle Scholar
  59. 54.
    Groen, M. B., Wijnberg, H.: ibid. 92, 6664 (1970)CrossRefGoogle Scholar
  60. 55.
    Yamada, K., Ogashiwa, S., Tanaka, H., Nakagawa, H., Kawazura, H.: Chem. Lett. 1981, 343Google Scholar
  61. 56.
    Fuchs, W., Niszel, I.: Chem. Ber. 60, 209 (1927)Google Scholar
  62. 57.
    Zander, M., Franke, W. H.: ibid. 102, 2728 (1969)Google Scholar
  63. 58.
    Rau, H., Schuster, O.: Angew. Chem. 88, 80 (1976)Google Scholar
  64. 59.
    Chatterjea, J. N., Banerji, K. D.: J. Ind. Chem. Soc. 47, 576 (1970)Google Scholar
  65. 60.
    Hogberg, H. E.: Acta Chem. Scand. 27, 2591 (1973)Google Scholar
  66. 61.
    Kagan, H., Moradpour, A., Nicoud, J. F., Balavoine, G., Tsoucaris, G.: J. Am. Chem. Soc. 93, 2353 (1971)CrossRefGoogle Scholar
  67. 62.
    Bernstein, W. J., Calvin, M., Buchardt, O.: ibid. 95, 527 (1973)CrossRefGoogle Scholar
  68. 63.
    Moradpour, A., Kagan, H., Baes, M., Morren, G., Martin, R. H.: Tetrahedron 31, 2139 (1975)CrossRefGoogle Scholar
  69. 64.
    Kagan, H., Moradpour, A., Nicoud, J. F., Balavoine, G., Martin, R. H., Cosijn, J. P.: Tetrahedron Lett. 1971, 2479Google Scholar
  70. 65.
    Bernstein, W. J., Calvin, M., Buchardt, O.: J. Am. Chem. Soc. 94, 494 (1972)CrossRefGoogle Scholar
  71. 66.
    Muszkat, K. A., Fischer, E.: J. Chem. Soc. B 1967, 662Google Scholar
  72. 67.
    Buchardt, O.: Angew. Chem. 86, 222 (1974)Google Scholar
  73. 68. a)
    Martin, R. H., Defay, N., Figeys, H. P., Le Van, K., Ruelle, J. J., Schurter, J. J.: Helv. Chim. Acta 55, 2241 (1972)CrossRefGoogle Scholar
  74. 68. b)
    de Jong, M. H., Laarhoven, W. H.: Recl. Trav. Chim. (Pays-Bas) 92, 673 (1973)Google Scholar
  75. 68. c)
    Somers, J. B. M., Laarhoven, W. H.: ibid. 99, 160 (1980)Google Scholar
  76. 69.
    Kagan, H. B., Fiaud, J. C., in: Topics in Stereochemistry (Ed. Eliel, E. L., Allinger, N. L., Wiley 1978), Vol. 10, p. 254Google Scholar
  77. 70.
    Bernstein, W. J., Calvin, M., Buchardt, O.: Tetrahedron Lett. 1972, 2195Google Scholar
  78. 71. a)
    Laarhoven, W. H., Cuppen, Th. J. H. M.: J. Chem. Soc. Chem. Comm. 1977, 47Google Scholar
  79. 71. b)
    Laarhoven, W. H., Cuppen, Th. J. H. M.: J. Chem. Soc. Perkin 2, 1978, 315Google Scholar
  80. 72.
    Nakazaki, M., Yamamoto, K., Fujiwara, K.: Chem. Lett. 1978, 863Google Scholar
  81. 73.
    Hibert, M., Solladie, G.: J. Org. Chem. 45, 5393 (1980)CrossRefGoogle Scholar
  82. 74.
    Nakazaki, M., Yamamoto, K., Fujiwara, K., Maeda, M.: J. Chem. Soc. Chem. Comm. 1979, 1086Google Scholar
  83. 75.
    Cochez, Y., Martin, R. H., Jespers, J.: Isr. J. Chem. 15, 29 (1977)Google Scholar
  84. 76.
    Vanest, J., Martin, R. H.: Recl. Trav. Chim. (Pays-Bas) 98, 113 (1979)Google Scholar
  85. 77.
    Cochez, Y., Jespers, J., Libert, V., Mislow, K., Martin, R. H.: Bull. Soc. Chim. Belg. 84, 1033 (1975)Google Scholar
  86. 78.
    Newman, M. S., Lutz, W. B., Lednicer, D.: J. Am. Chem. Soc. 77, 3420 (1955)CrossRefGoogle Scholar
  87. 79.
    Wijnberg, H., Groen, M. B., Schadenberg, H.: J. Org. Chem. 36, 2797 (1971)CrossRefGoogle Scholar
  88. 80.
    Martin, R. H., Marchant, M. J.: Tetrahedron 30, 343 (1974)CrossRefGoogle Scholar
  89. 81.
    Klemm, L. H., Reed, D.: J. Chrom. 3, 364 (1960)CrossRefGoogle Scholar
  90. 82.
    Teuber, H. J., Vogel, L.: Chem. Ber. 103, 3319 (1970)Google Scholar
  91. 83. a)
    Nakazaki, M., Yamamoto, K., Maeda, M.: J. Org. Chem. 46, 1985 (1981)CrossRefGoogle Scholar
  92. 83. b)
    Nakazaki, M., Yamamoto, K., Maeda, M.: Chem. Lett. 1980, 1553Google Scholar
  93. 84.
    Okamoto, Y., Honda, S., Okamoto, I., Yuki, H., Murata, S., Noyori, R.: J. Am. Chem. Soc. 103, 6971 (1981)CrossRefGoogle Scholar
  94. 85. a)
    Mikes, F., Boshart, G., Gil-Av, E.: J. Chem. Soc. Chem. Comm. 1976, 99Google Scholar
  95. 85. b)
    Mikes, F., Boshart, G., Gil-Av, E.: J. Chrom. 122, 205 (1976)CrossRefGoogle Scholar
  96. 86.
    Numan, H., Helder, R., Wijnberg, H.: Recl. Trav. Chim. (Pays-Bas) 95, 211 (1976)Google Scholar
  97. 87.
    Nakagawa, H., Ogashiwa, S., Tanaka, H., Yamada, K., Kawazura, H.: Bull. Chem. Soc. Japan 54, 1903 (1981)Google Scholar
  98. 88. a)
    Mikes, F., Boshart, G.: J. Chem. Soc. Chem. Comm. 1978, 173Google Scholar
  99. 88. b)
    Mikes, F., Boshart, G.: J. Chrom. 149, 455 (1978)CrossRefGoogle Scholar
  100. 89.
    Wijnberg, H., Lammertsma, K.: J. Am. Chem. Soc. 95, 7913 (1973)CrossRefGoogle Scholar
  101. 90.
    Nakagawa, H., Tanaka, H., Yamada, K., Kawazura, H.: J. Phys. Chem. 86, 2311 (1982)CrossRefGoogle Scholar
  102. 91.
    Tanaka, H., Nakagawa, H., Yamada, K., Kawazura, H.: Bull. Chem. Soc. Japan 54, 3665 (1981)Google Scholar
  103. 92. a)
    Kim, Y. H., Tishbee, A., Gil-Av, E.: J. Am. Chem. Soc. 102, 5915 (1980)CrossRefGoogle Scholar
  104. 92. b)
    Kim, Y. H., Tishbee, A., Gil-Av, E.: Science 213, 1883 (1981)Google Scholar
  105. 93.
    Lochmuller, C. H., Jensen, E. C.: J. Chrom. 216, 333 (1981)CrossRefGoogle Scholar
  106. 94.
    Kim, Y. H., Balan, A., Tishbee, A., Gil-Av, E.: J. Chem. Soc. Chem. Comm. 1982, 1336Google Scholar
  107. 95. a)
    Barron, L. D.: J. Chem. Soc. Farad. Trans 2 71, 293 (1975)CrossRefGoogle Scholar
  108. 95. b)
    Barron, L. D.: J. Am. Chem. Soc. 96, 6761 (1974)CrossRefGoogle Scholar
  109. 96.
    Groen, M. B., Wijnberg, H.: J. Am. Chem. Soc. 93, 2968 (1971)CrossRefGoogle Scholar
  110. 97.
    Mason, S. F., Brickell, W. S., Browns, A., Kemp, C. M.: J. Chem. Soc. (A) 1971, 756Google Scholar
  111. 98.
    Hug, W., Wagniere, G.: Tetrahedron 28, 1241 (1972)CrossRefGoogle Scholar
  112. 99. a)
    Lightner, D. A., Hefelfinger, D. T., Frank, G. W., Powers, T. W., Trueblood, K. N.: Nature 232, 124 (1971)PubMedGoogle Scholar
  113. 99. b)
    Lightner, D. A., Hefelfinger, D. T., Frank, G. W., Powers, T. W., Trueblood, K. N.: J. Am. Chem. Soc. 94, 3492 (1972)CrossRefGoogle Scholar
  114. 100.
    Tribout, J., Martin, R. H., Doyle, M., Wijnberg, H.: Tetrahedron Lett. 1972, 2839Google Scholar
  115. 101.
    Newman, M. S., Darlak, R. S., Tsai, L. L.: J. Am. Chem. Soc. 89, 6191 (1967)CrossRefGoogle Scholar
  116. 102.
    Yamada, K., Tanaka, H., Nakagawa, H., Ogashiwa, S., Kawazura, H.: Bull. Chem. Soc. Japan 55, 500 (1982)Google Scholar
  117. 103.
    Martin, R. H., Marchant, M. J.: Tetrahedron 30, 347 (1974)CrossRefGoogle Scholar
  118. 104.
    Lindner, H. J.: ibid. 31, 281 (1975)CrossRefGoogle Scholar
  119. 105.
    Borkent, J. H., Laarhoven, W. H.: ibid. 34, 2565 (1978)CrossRefGoogle Scholar
  120. 106.
    Martin, R. H., Marchant, M. J.: Tetrahedron Lett. 1972, 3707Google Scholar
  121. 107.
    Martin, R. H., Defay, N., Figeys, H. P., Flammang-Barbieux, M., Cosijn, J. P., Gelbcke, M., Schurter, J. J.: Tetrahedron 25, 4985 (1969)CrossRefGoogle Scholar
  122. 108.
    Haigh, C. W., Mallion, R. B.: Mol. Phys. 22, 945 (1971)Google Scholar
  123. 109.
    Laarhoven, W. H., Nivard, R. J. F.: Tetrahedron 28, 1803 (1972)CrossRefGoogle Scholar
  124. 110.
    Defay, N.: Org. Magn. Resonance 6, 221 (1974)CrossRefGoogle Scholar
  125. 111.
    Haigh, C. W., Mallion, R. B.: Mol. Phys. 22, 955 (1971)Google Scholar
  126. 112.
    Somers, J. B. M., Borkent, J. H., Laarhoven, W. H.: Recl. Trav. Chim. (Pays-Bas) 100, 110 (1981)Google Scholar
  127. 113.
    Diesveld, J. W., Borkent, J. H., Laarhoven, W. H.: Tetrahedron 38, 1803 (1982)CrossRefGoogle Scholar
  128. 114.
    van den Hark, Th. E. M., Noordik, J. H., Beurskens, P. T.: Cryst. Struct. Comm. 3, 443 (1974)Google Scholar
  129. 115.
    Sato, T., Akabori, S., Muto, S., Hata, K.: Tetrahedron 24, 5557 (1968)CrossRefGoogle Scholar
  130. 116.
    Martin, R. H., Defay, N., Zimmermann, D.: Tetrahedron Lett. 1971, 1871Google Scholar
  131. 117.
    Martin, R. H., Schurter, J. J.: Tetrahedron 28, 1749 (1972)CrossRefGoogle Scholar
  132. 118.
    Boekelheide, V., Schmidt, W.: Chem. Phys. Lett. 17, 410 (1972)CrossRefGoogle Scholar
  133. 119.
    Heilbronner, E., Maier, J. P.: Helv. Chim. Acta 57, 151 (1974)CrossRefGoogle Scholar
  134. 120.
    Obenland, S., Schmidt, W.: J. Am. Chem. Soc. 97, 6633 (1975)CrossRefGoogle Scholar
  135. 121.
    Deb, B. M., Kavu, G.: Can. J. Chem. 58, 258 (1980)Google Scholar
  136. 122.
    Clar, E.: Polycyclic Hydrocarbons, Acad. Press New York 1964, Vol. 1Google Scholar
  137. 123.
    Birks, J. B., Birch, D. J. S., Cordemans, E., van der Donckt, E.: Chem. Phys. Lett. 43, 33 (1976)CrossRefGoogle Scholar
  138. 124.
    Boschi, R., Clar, E., Schmidt, W.: J. Chem. Phys. 60, 4406 (1974)CrossRefGoogle Scholar
  139. 125.
    van der Donckt, E., Nasielski, E., Greenleaf, J., Birks, J. B.: Chem. Phys. Lett. 2, 409 (1968)CrossRefGoogle Scholar
  140. 126.
    Brown, J. M., Field, I. P., Sidebottom, P. J.: Tetrahedron Lett. 22, 4867 (1981)CrossRefGoogle Scholar
  141. 127.
    Balan, A., Gottlieb, H. E.: J. Chem. Soc. Perkin 2 1981, 350Google Scholar
  142. 128.
    Wijnberg, H., Groen, M. B.: J. Chem. Soc. D 1969, 964Google Scholar
  143. 129.
    Martin, R. H., Morren, G., Schurter, J. J.: Tetrahedron Lett. 1969, 3683Google Scholar
  144. 130.
    Sapir, M., van der Donckt, E.: Chem. Phys. Lett. 36, 108 (1975)CrossRefGoogle Scholar
  145. 131.
    Kim, S. S., Weissman, S. I.: J. Am. Chem. Soc. 101, 5863 (1979)CrossRefGoogle Scholar
  146. 132.
    Weissman, S. I., Chang, R.: ibid. 94, 8683 (1972)CrossRefGoogle Scholar
  147. 133.
    Fey, H. J., Kurreck, H., Lubitz, W.: Tetrahedron 35, 905 (1979)CrossRefGoogle Scholar
  148. 134.
    Tanaka, H., Ogashiwa, S., Kawazura, H.: Chem. Lett. 1981, 585Google Scholar
  149. 135.
    Allendoerfer, R. D., Chang, R.: J. Magn. Resonance 5, 273 (1971)Google Scholar
  150. 136.
    Laarhoven, W. H., Brus, G. J. M.: J. Chem. Soc. B 1971, 1433Google Scholar
  151. 137.
    Streitwieser, A., in: Molecular Orbital Theory for Organic Chemists, John Wiley, New York 1961, p. 175Google Scholar
  152. 138.
    Diesveld, J. W., Borkent, J. H., Laarhoven, W. H.: Recl. Trav. Chim. (Pays-Bas) 99, 391 (1980)Google Scholar
  153. 140.
    Stulen, G., Visser, G. J.: J. Chem. Soc. Chem. Comm. 1969, 965Google Scholar
  154. 141.
    De Rango, C., Tsoucaris, G., Declerq, J. P., Germain, G., Putzeys, J. P.: Cryst. Struct. Comm. 2, 189 (1973)Google Scholar
  155. 142.
    Frank, G. W., Hefelfinger, D. T., Lightner, D. A.: Acta Crystallogr. Sect. B 29, 223 (1973)CrossRefGoogle Scholar
  156. 143.
    van der Hark, Th. E. M., Noordik, J. H.: Cryst. Struct. Comm. 2, 643 (1973)Google Scholar
  157. 144.
    Marsh, W., Dunitz, J. D.: Bull. Soc. Chim. Belg. 88, 847 (1979)Google Scholar
  158. 145.
    Navaza, J., Tsoucaris, G., Le Bas, G., Navaza, A., De Rango, C.: ibid. 88, 863 (1979)Google Scholar
  159. 146.
    Kuroda, R.: J. Chem. Soc. Perkin 2 1982, 789Google Scholar
  160. 147.
    Doesburg, H. M.: Cryst. Struct. Comm. 9, 137 (1980)Google Scholar
  161. 148.
    Lindner, H. J., Kitschke, B.: Bull. Soc. Chim. Belg. 88, 831 (1979)Google Scholar
  162. 149.
    Dewan, J. C.: Acta Crystallogr. Sct. B 37, 1421 (1981)CrossRefGoogle Scholar
  163. 150.
    Beurskens, P. T., Beurskens, G., van den Hark, T. E. M.: Cryst. Struct. Comm. 5, 241 (1976)Google Scholar
  164. 151.
    van den Hark, T. E. M., Beurskens, P. T.: ibid. 247 (1976)Google Scholar
  165. 152.
    Le Bas, G., Navaza, A., Mauguen, Y., De Rango, C.: ibid. 5, 357 (1976)Google Scholar
  166. 153.
    Le Bas, G., Navaza, A., Knossow, M., De Rango, C.: ibid. 5, 713 (1976)Google Scholar
  167. 154.
    Konno, M., Saito, Y., Yamada, K., Kawazura, H.: Acta Cryst. Section B 36, 1680 (1980)CrossRefGoogle Scholar
  168. 155.
    Green, B. S., Knossow, M.: Science 214, 795 (1981)Google Scholar
  169. 156.
    Ramdas, S., Thomas, J. M., Jordan, M. E., Eckhardt, C. J.: J. Phys. Chem. 85, 2421 (1981)CrossRefGoogle Scholar
  170. 157.
    Herraez, M. A., Sanchez, F.: An. Soc. Esp. Fis. Quim. 61 B, 953 (1965)Google Scholar
  171. 158.
    Kitaigorodskii, A. I., Dashevskii, V. G.: Tetrahedron 24, 5917 (1968)CrossRefGoogle Scholar
  172. 159.
    Dougherty, R. C.: J. Am. Chem. Soc. 90, 5788 (1968)CrossRefGoogle Scholar
  173. 160.
    Martin, R. H., Jespers, J., Defay, N.: Helv. Chim. Acta 58, 776 (1975)CrossRefGoogle Scholar
  174. 161.
    Declerq, J. P., Germain, G., van Meerssche, M., Debaerdemacker, T.: Actacrystallogr. B 32, 335 (1976)Google Scholar
  175. 162.
    Numan, H., Wijnberg, H.: Tetrahedron Lett. 1975, 1097Google Scholar
  176. 163.
    Martin, R. H., Jespers, J., Defay, N.: ibid. 1975, 1093Google Scholar
  177. 164.
    Borkent, J. H., Rouwette, P. H. F. M., Laarhoven, W. H.: Tetrahedron 34, 2569 (1978)CrossRefGoogle Scholar
  178. 165.
    For a review see: Balaban and Menitzesen in: Friedel Crafts and Related Reactions, Olah Ed. Interscience Publishers Inc. New York 1963, Vol. II, p. 979Google Scholar
  179. 166.
    Dopper, J. H., Oudman, D., Wijnberg, H.: J. Org. Chem. 40, 3398 (1975)CrossRefGoogle Scholar
  180. 167.
    Dopper, J. H., Wijnberg, H.: ibid. 40, 1957 (1975)CrossRefGoogle Scholar
  181. 168.
    Jespers, J., Defay, N., Martin, R. H.: Tetrahedron 33, 2141 (1977)CrossRefGoogle Scholar
  182. 169.
    op den Brouw, P. M., Laarhoven, W. H.: Recl. Trav. Chim. (Pays-Bas) 97, 265 (1978)Google Scholar
  183. 170.
    Archer, W. J., El Din Shafig, Y., Taylor, R.: J. Chem. Soc. Perkin 2 1981, 675Google Scholar
  184. 171.
    Lehman, P. G., Wijnberg, H.: Aust. J. Chem. 27, 315 (1974)Google Scholar
  185. 172.
    Mallory, F. B., Mallory, C. W.: J. Org. Chem. 48, 526 (1983)CrossRefGoogle Scholar
  186. 173.
    Wijnberg, H., Nieuwpoort, W. C., Jonkman, H. T.: Tetrahedron Lett. 1973, 4623Google Scholar
  187. 174.
    Laarhoven, W. H., van Broekhoven, J. A. M.: ibid. 1970, 73Google Scholar
  188. 175.
    Soubrier-Payen, B.: Thesis, Louvain la Neuve, 1978Google Scholar
  189. 176.
    van Meerssche, M., Germain, G., Declerq, J. P., Soubrier-Payen, B., Figeys, H. P., Vanommeslaeghe, P.: Acta Crystallogr. B 37, 1218 (1981)Google Scholar
  190. 177.
    Katz, J., Pesti, J.: J. Am. Chem. Soc. 104, 346 (1982)CrossRefGoogle Scholar
  191. 178.
    Nakazaki, M., Yamamoto, K., Ikeda, T., Kisuki, T., Okamoto, Y.: J. Chem. Soc. Chem. Comm. 787 (1983)Google Scholar
  192. 179.
    Martin, R. H., Morian, J., Defay, N.: Tetrahedron 30, 179 (1974)CrossRefGoogle Scholar
  193. 180.
    Defay, N., Martin, R. H.: Bull. Soc. Chim. Belg. 93, 313 (1984)Google Scholar

Copyright information

© Springer-Verlag 1984

Authors and Affiliations

  • Wim H. Laarhoven
    • 1
  • Wim J. C. Prinsen
    • 1
  1. 1.Laboratory for Organic ChemistryCatholic University of Nijmegen, ToernooiveldNijmegenThe Netherlands

Personalised recommendations