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Bicyclo[3,3,1]nonanes and Related Compounds

  • G. L. Buchanan

Abstract

The bicyclo[3,3,l]nonane ring system I, shown here both in plan and in perspective, has been known for about seventy years, and work on this, and related bicyclic systems, has uncovered and illustrated many significant chemical principles; yet it has never been adequately reviewed.

Keywords

Concentrate Sulphuric Acid Bicyclic Compound Boat Form Bicyclic Product Patchouli Alcohol 
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.

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References

  1. 1.
    Adesogan, E. K., Bevan, C. W. L., Powell, J. W. and Taylor, D. A. W. (1966) J. Chem. Soc. (C) 2127.Google Scholar
  2. 2.
    Appleton, R. A. and Graham, S. H. (1965)Chem. Communications 297.Google Scholar
  3. 3.
    Appleton, R. A., Dixon, J. R., Evans, J. M. and Graham, S. H. (1967) Tetrahedron 23, 805.Google Scholar
  4. 4.
    Appleton, R. A., Egan, C., Evans, J. M., Graham, S. H. and Dixon, J. R. (1968) J. Chem. Soc. (C) 1110.Google Scholar
  5. 5.
    Appleton, R. A., Baggaley, K. H., Egan, C., Davies, J. M., Graham, S. H. and Lewis, D. O. (1968) J. Chem. Soc. (C) 2032.Google Scholar
  6. 6.
    Baggaley, K. H., Dixon, J. R., Evans, J. M. and Graham, S. H. (1967) Tetrahedron 23, 299.Google Scholar
  7. 7.
    Baggaley, K. H., Evans, W. H. and Graham, S. H. (1968) Tetrahedron 24, 3445.Google Scholar
  8. 8.
    Bailey, D. M., Bowers, J. E. and Gutsche, C. D. (1963) J. Org. Chem. 28, 607, 610.Google Scholar
  9. 9.
    Baisted, D. J. and Whitehurst, J. S. (1961) J. Chem. Soc. 4089.Google Scholar
  10. 10.
    Baker, W. and Leeds, W. G. (1948) J. Chem. Soc. 974.Google Scholar
  11. 11.
    Barbulescu, N. and Govela, M. (1963) Chem. Abstr. 59, 1506b [(1961) Analele Univ. C.I. Parhon, Ser. Stiint, Nat. 10, 151].Google Scholar
  12. 12.
    Bardhan, J. C. and Banerjee, R. C. (1956) J. Chem. Soc. 1809.Google Scholar
  13. 13.
    Becker, D. and Loewenthal, H. J. E. (1965)Chem. Communications 149.Google Scholar
  14. 14.
    Becker, D., and Loewenthal, H. J. E. (1965) J. Chem. Soc. 1338.Google Scholar
  15. 15.
    Beckmann, S. and Ling, O. S. (1961) Chem. Ber. 94, 1899.Google Scholar
  16. 16.
    Bellamy, L. J. (1968) Advances in Infrared Group Frequencies, Methuen, London, p. 128.Google Scholar
  17. 17.
    Birch, A. J. and Hill, J. S. (1966) J. Chem. Soc. (G) 419.Google Scholar
  18. 18.
    Birch, S. F., Cullum, T. V., Dean, R. A, and Denyer, R. L. (1952) Nature, Lond. 170, 629.Google Scholar
  19. 19.
    Bottger, O. (1937) Chem. Ber. 70, 314.Google Scholar
  20. 20.
    Bredt, J. (1924) Liebigs Ann. 437, 1.Google Scholar
  21. 21.
    Brown, W. A. C., Martin, J. and Sim, G. A. (1965) J. Chem. Soc. 1844.Google Scholar
  22. 22.
    Buchanan, G. L., Maxwell, C. and Henderson, W. (1965) Tetrahedron 21, 3273.Google Scholar
  23. 23.
    Buchanan, G. L., Millop, A. and Raphael, R. A. (1965) J. Chem. Soc. 833.Google Scholar
  24. 24.
    Buchanan, G. L., Ferguson, G., Lawson, A. M. and Pollard, D. R. (1966) Tetrahedron Letters 5303.Google Scholar
  25. 25.
    Buchanan, G. L. and May, G. W. (1966) Tetrahedron 22, 1521.Google Scholar
  26. 26.
    Buchanan, G. L., Curran, A. C. W., Mrae, J. M. and May, G. W. (1967) Tetrahedron 23, 4729.Google Scholar
  27. 27.
    Buchi, G., Biemann, K., Vittimberger, B. and Stoll, M. (1956) J. Amer. Chem. Soc. 78, 2622.Google Scholar
  28. 28.
    Buchi, G., Erickson, R. E. and Wakabayashi, N. (1961) J. Amer. Chem. Soc. 83, 927.Google Scholar
  29. 29.
    Buchi, G. and Meod, W. D. (1962) J. Amer. Chem. Soc. 84, 3205.Google Scholar
  30. 30.
    Buchta, E. and Billenstein, S. (1964) Naturwissenschaften 51 (16), 383.Google Scholar
  31. 31.
    Clunie, J. S., and Robertson, J. M. (1960)Proc. Chem. Soc. 82.Google Scholar
  32. 32.
    Clunie, J. S. and Robertson, J. M. (1961)J. Chem. Soc. 4382.Google Scholar
  33. 33.
    Colvin, E. W. and Parker, W. (1965) J. Chem. Soc. 5764.Google Scholar
  34. 34.
    Connolly, J. D., Henderson, R., Mrindle, R., Overton, K. H. and Bhacca, N. S. (1965) J. Chem. Soc. 6935.Google Scholar
  35. 35.
    Connolly, J. D., Mrindle, R. and Overton, K. H. (1968) Tetrahedron 24, 1489.Google Scholar
  36. 36.
    Connolly, J. D., Mrindle, R. and Overton, K. H. (1968) Tetrahedron 24, 1497.Google Scholar
  37. 37.
    Connolly, J. D., Mrindle, R. and Warnock, W. D. C. (1968) Tetrahedron 24, 1507.Google Scholar
  38. 38.
    Cope, A. C., Fawcett, E. S. and Munn, G. (1950), J. Amer. Chem. Soc. 72, 3399.Google Scholar
  39. 39.
    Cope, A. C. and Hermann, E. C. (1950) J. Amer. Chem. Soc. 72, 3405.Google Scholar
  40. 40.
    Cope, A. C. and Synerholm, M. E. (1950) J. Amer. Chem. Soc. 72, 5228.Google Scholar
  41. 41.
    Cope, A. C. and Graham, E. S. (1951) J. Amer. Chem. Soc. 73, 4702.Google Scholar
  42. 42.
    Cope, A. C., Graham, E. S. and Marshall, D. J. (1954), J. Amer. Chem. Soc. 76, 6159.Google Scholar
  43. 43.
    Cope, A. C., Nealy, D. L., Scheiner, P. and Wood, G. (1965) J. Amer. Chem. Soc. 87, 3130.Google Scholar
  44. 44.
    Corey, E. J., Carey, F. A. and Winter, R. A. E. (1965) J. Amer. Chem. Soc. 87, 934.Google Scholar
  45. 45.
    Corey, E. J. and Nozoe, S. (1965) J. Amer. Chem. Soc. 87, 5728.Google Scholar
  46. 46.
    Danishefsky, S., Koppel, G. and Levine, R. (1968) Tetrahedron Letters 2257.Google Scholar
  47. 47.
    Dauben, W. G. and Marland, J. W. (1960) J. Amer. Chem. Soc. 82, 4245.Google Scholar
  48. 48.
    Dauben, W. G., Boswell, G. H. and Templeton, W. H. (1961) J. Amer. Chem. Soc. 83, 5006.Google Scholar
  49. 49.
    Dean, C. S., Dixon, J. R., Graham, S. H. and Lewis, D. O. (1968) J. Chem. Soc. (C) 1491.Google Scholar
  50. 50.
    Dobler, M., Dunitz, J. D., Gubler, B., Weber, H. P., Buehi, G. and Padilla, O. J. (1963) Proc. Ghem. Soc. 383.Google Scholar
  51. 51.
    Doyle, P., Maclean, I. R., Murray, R. D. H., Parker, W. and Raphael, R. S. (1965) J. Ghem. Soc. 1344.Google Scholar
  52. 52.
    Eakin, M. A., Martin, J., Parker, W., Egan, C. and Graham, S. H. (1968) Ghem. Communications 337.Google Scholar
  53. 53.
    Eakin, M. A., Martin, J. and Parker, W. (1968)Ghem. Communications 298.Google Scholar
  54. 54.
    Eglinton, G., Martin, J. and Parker, W. (1965) J. Ghem. Soc. 1243.Google Scholar
  55. 55.
    Eistert, B., Haupter, F. and Schank, K. (1963) Liebigs Ann. 665, 55.Google Scholar
  56. 56.
    Eliel, E. L. (1962) Stereochemistry of Carbon Compounds, McGraw-Hill, New York, p. 296.Google Scholar
  57. 57.
    Erman, W. F. and Kretsehmar, H. C. (1967) J. Amer. Ghem. Soc. 89, 3842.Google Scholar
  58. 58.
    Erman, W. F. and Kretsehmar, H. C. (1968) J. Org. Ghem. 33, 1545.Google Scholar
  59. 59.
    Fawcett, F. S. (1950) Ghem. Rev. 47, 219.Google Scholar
  60. 60.
    Fell, B., Seidl, W. and Asinger, F. (1968)Tetrahedron Letters 1003.Google Scholar
  61. 61.
    Ferguson, G., Hawley, D. M., Millop, T. F. W., Martin, J., Parker, W. and Doyle, P. (1967) Chem. Communications 1123.Google Scholar
  62. 62.
    Ferguson, G., Macrossan, W. D. K., Martin, J. and Parker, W. (1967) Chem. Communications 102.Google Scholar
  63. 63.
    Ferris, J. P. and Miller, N. C. (1963) J. Amer. Chem. Soc. 85, 1325.Google Scholar
  64. 64.
    Ferris, J. P. and Miller, N. C. (1966) J. Amer. Chem. Soc. 88, 3522.Google Scholar
  65. 65.
    Foote, C. S. (1964) J. Amer. Chem. Soc. 86, 1853.Google Scholar
  66. 66.
    Foote, C. S. and Woodward, R. B. (1964) Tetrahedron 20, 687.Google Scholar
  67. 67.
    Fort, R. C. and Schleyer, P. von R. (1966) in Advances in Alicyclic Chemistry, edited by Hart, H. and Karabatsos, G. J. Vol. I, Academic Press, New York, p. 283.Google Scholar
  68. 68.
    Freeman, S. K. (1965) Interpretive Spectroscopy, Reinhold, New York, p.111.Google Scholar
  69. 69.
    Fujimoto, G. (1951) J. Amer. Chem. Soc. 73, 1856.Google Scholar
  70. 70.
    Fujimoto, G. and Zwahlen, K. D. (1960) J. Org. Chem. 25, 445.Google Scholar
  71. 71.
    Fujimoto, G. and Parlos, J. (1965)Tetrahedron Letters 4477.Google Scholar
  72. 72.
    Ghatak, V. R. and Chakravarty, J. (1966)Tetrahedron Letters 2449.Google Scholar
  73. 73.
    Gould, E. S. (1959) Mechanism and Structure in Organic Chemistry, Rinehart & Winston, New York, p. 325.Google Scholar
  74. 74.
    Grob, C. A. and Hostynek, J. (1963) Helv. Chim. Acta 46, 2212.Google Scholar
  75. 75.
    Gutsche, D., Smith, T. D., Sloan, M. F., van Ufford, J. J. Q. and Jorgan, D. E. (1958) J. Amer. Ghem. Soc. 80, 4117.Google Scholar
  76. 76.
    75.Hargreaves, J. R. and Hickmott, P. W. (1966) Tetrahedron Letters 4173.Google Scholar
  77. 77.
    Hellmann, H. M., Jerussi, R. A. and Lancaster, J. (1967) J. Org. Chem. 32, 2148.Google Scholar
  78. 78.
    Hickmott, P. W. and Hargreaves, J. R. (1967) Tetrahedron 23, 3151.Google Scholar
  79. 79.
    House, H. O. and Muller, H. C. (1962) J. Org. Chem. 27, 4436.Google Scholar
  80. 80.
    House, H. O. (1965) Modern Synthetic Reactions, W. A. Benjamin, New York, p. 210.Google Scholar
  81. 81.
    Jefford, C. W., Waegell, B. and Ramay, K. (1965) J. Amer. Chem. Soc. 87, 2191.Google Scholar
  82. 82.
    Johnston, W. S., Korst, J. A., Clement, R. A. and Dutta, J. (1960) J. Amer. Chem. Soc. 82, 614.Google Scholar
  83. 83.
    Julia, S. A. (1954) Bull. Soc. Chim. Fr. 780.Google Scholar
  84. 84.
    Knoevenagel, E. (1894) Liebigs Ann. 281, 39; (1903)Chem. Ber. 36, 2144.Google Scholar
  85. 85.
    Kraus, W. and Rothenwohrer, W. (1968)Tetrahedron Letters 1007.Google Scholar
  86. 86.
    Kraus, W. and Rothenwohrer, W. (1968)Tetrahedron Letters 1013.Google Scholar
  87. 87.
    Landa, S. and Kamycek, Z. (1959) Coll. Czech. Chem. Comm. 24, 1320.Google Scholar
  88. 88.
    Laszlo, I. (1965) Bee. Trav. Chim. 84, 251.Google Scholar
  89. 89.
    Lawson, A. M. (1966) Ph.D. Thesis, Glasgow University.Google Scholar
  90. 90.
    Lel, N. A. and Spurloek, L. A. (1964) J. Org. Chem. 29, 1337.Google Scholar
  91. 91.
    Lel, N. A. and Spurloek, L. A. (1964) Tetrahedron 20, 215.Google Scholar
  92. 92.
    Loewenthal, H. J. E. and Neuwirth, Z. (1967) J. Org. Chem. 32, 517.Google Scholar
  93. 93.
    Maclay, G. W. (1965) Ph.D. Thesis, Glasgow University.Google Scholar
  94. 94.
    Mhail, A. T. and Sim, G. A. (1964)Tetrahedron Letters 2599.Google Scholar
  95. 95.
    Macrossan, W. D. K., Martin, J. and Parker, W. (1965) Tetrahedron Letters 2589.Google Scholar
  96. 96.
    Macrossan, W. D. K. and Ferguson, G. (1968)J. Chem. Soc. (B) 242.Google Scholar
  97. 97.
    Marshall, J. A. and Scanio, C. J. V. (1965) J. Org. Chem. 30, 3019.Google Scholar
  98. 98.
    Marshall, J. A. and Schaeffer, D. J. (1965) J. Org. Chem. 30, 3642.Google Scholar
  99. 99.
    Marshall, J. A. and Partridge, J. J. (1966)Tetrahedron Letters 2545.Google Scholar
  100. 100.
    Marshall, J. A. and Faubl, H. (1967) J. Amer. Chem. Soc. 89, 5965.Google Scholar
  101. 101.
    Martin, J., Parker, W. and Raphael, R. A. (1964) J. Chem. Soc. 289.Google Scholar
  102. 102.
    Martin, J., Parker, W., Shroot, B. and Stewart, T. (1967) J. Chem. Soc. 101.Google Scholar
  103. 103.
    Maxwell, C. (1965) Ph.D. Thesis, Glasgow University.Google Scholar
  104. 104.
    Mayer, R., Wenschuh, G. and Topelmann, W. (1958) Chem. Ber. 91, 1616.Google Scholar
  105. 105.
    Meerwein, H. (1922) J. Prakt. Chem. (2) 104, 161.Google Scholar
  106. 106.
    Meinwald, J., Shelton, J. C., Buchanan, G. L. and Courtin, A. (1968) J. Org. Chem. 33, 99.Google Scholar
  107. 107.
    Murray, R. D. H., Parker, W., Raphael, R. A. and Jhaveri, D. B. (1962) Tetrahedron 18, 55.Google Scholar
  108. 108.
    Opitz, G. and Holtmann, H. (1965) Liebigs Ann. 684, 79.Google Scholar
  109. 109.
    Pitha, J., Plesek, J. and Horak, M. (1961) Coll. Czech. Chem. Comm. 26, 1209.Google Scholar
  110. 110.
    Prelog, Y. and Seiwerth, R. (1941) Chem. Ber. 74, 1644.Google Scholar
  111. 111.
    Prelog, V., Barman, P. and Zimmermann, M. (1949) Helv. Chim. Acta 32, 1284.Google Scholar
  112. 112.
    Prelog, Y. and Zimmermann, M. (1949) Helv. Chim. Acta 32, 2360.Google Scholar
  113. 113.
    Prelog, Y. (1950) J. Chem. Soc. 420.Google Scholar
  114. 114.
    Rabe, P., Ehrenstein, R. E. and Jahr, M. (1908) Liebigs Ann. 360, 265.Google Scholar
  115. 115.
    Sands, R. D. (1963) J. Org. Chem. 28, 1710.Google Scholar
  116. 116.
    Schaeffer, J. P., Endres, L. S. and Moran, M. D. (1967) J. Org. Chem. 32, 3963.Google Scholar
  117. 117.
    Schut, R. N. and Liu, T. M. H. (1965) J. Org. Chem. 30, 2845.Google Scholar
  118. 118.
    Spencer, T. A., Newton, M. D. and Baldwin, S. W. (1964) J. Org. Chem. 29, 787.Google Scholar
  119. 119.
    Stetter, H., Bander, O. E. and Neumann, W. (1956) Chem. Ber. 89, 1922.Google Scholar
  120. 120.
    Stetter, H. and Mayer, J. (1959) Chem. Ber. 92, 2664.Google Scholar
  121. 121.
    Stetter, H., Held, H. and Schulte-Oestrich, A. (1962) Chem. Ber, 95. 1687.Google Scholar
  122. 122.
    Stetter, H., Held, H. and Mayer, J. (1962) Liebigs Ann. 658, 151.Google Scholar
  123. 123.
    Stetter, H., and Taeke, P. (1963) Ghem. Ber. 96, 694.Google Scholar
  124. 124.
    Stetter, H., Taeke, P. and Gartner, J. (1964) Chem. Ber. 97, 3480.Google Scholar
  125. 125.
    Stetter, H., Gartner, J. and Taeke, P. (1965) Angew. Ghemie (Internat. Ed.) 4, 153.Google Scholar
  126. 126.
    Stetter, H. and Gartner, J. (1966) Ghem. Ber. 99, 925.Google Scholar
  127. 127.
    Stetter, H. and Thomas, H. G. (1966) Ghem. Ber. 99, 920.Google Scholar
  128. 128.
    Stetter, H., Gartner, J. and Taeke, P. (1966) Ghem. Ber. 99, 1435.Google Scholar
  129. 129.
    Stetter, H. and Thomas, H. G. (1968) Chem. Ber. 101, 1115.Google Scholar
  130. 130.
    Stoll, M., Willhalen, B. and Buchi, G. (1955) Helv. Chim. Acta 38, 1573.Google Scholar
  131. 131.
    Stork, G. and Landesmann, H. K. (1956) J. Amer. Chem. Soc. 78, 5129.Google Scholar
  132. 132.
    Stork, G., Kretehmer, R. A. and Schlessinger, R. H. (1968)J. Amer. Chem. Soc. 90, 1647.Google Scholar
  133. 133.
    Valenta, Z., Yoshimura, H., Rogers, E. F., Ternbah, M. and Wiesner, K. (1960) Tetrahedron 10, 26.Google Scholar
  134. 134.
    Walls, F., Padilla, J., Joseph-Nathan, P., Giral, F. and Romo, J. (1965) Tetrahedron Letters 1577. Google Scholar
  135. 135.
    Warnhoff, E. W., Wong, C. M. and Tai, W. T. (1967) J. Org. Chem. 32, 2664.Google Scholar
  136. 136.
    Webb, N. C. and Becker, M. R. (1967) J. Chem. Soc. (B) 1317.Google Scholar
  137. 137.
    Wichterle, O. and Hudlicky, M. (1947) Coll. Czech. Chem. Comm. 12, 101.Google Scholar
  138. 138.
    Wichterle, O. (1948) Coll. Czech. Chem. Comm. 13, 300.Google Scholar
  139. 139.
    Wiseman, J. R. (1967) J. Amer. Chem. Soc. 89, 5966.Google Scholar
  140. 140.
    Yogev, A. and Mazur, Y. (1965) J. Amer. Chem. Soc. 87, 3520.Google Scholar
  141. 141.
    Yoshimura, H., Valenta, Z. and Wiesner, K. (1960) Tetrahedron Letters 12, 14.Google Scholar
  142. 142.
    Zbinden, R. and Hall, H. K. (1960) J. Amer. Chem. Soc. 82, 1215.Google Scholar
  143. 143.
    Ziegler, K. and Wilms, H. (1950) Liebigs Ann. 567, 1.Google Scholar
  144. 144.
    Ref. 100, footnote 4Google Scholar

Copyright information

© Logos Press Limited 1969

Authors and Affiliations

  • G. L. Buchanan
    • 1
  1. 1.Reader in Organic ChemistryUniversity of GlasgowGlasgow, W.2Scotland

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