By Cyclodehydration to Centropolyindanes: Development of a Novel Class of Indane Hydrocarbons with Three-dimensional Molecular Frameworks Using a Classical Synthetic Tool

Synlett

Volumn 1996, Issue 10, 1996, Pages 949-965

  Kuck, Dietmar ^a,b,c,d  

^a BIELEFELD UNIVERSITY   (Germany)

^b UNIVERSITY OF PADERBORN   (Germany)

^c UNIVERSITY OF HAMBURG   (Germany)

^d UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003057673     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5632     Document Type: Article

References (146)

1. Campbell, N.; Davison, P. S.; Heller, H. G. J. Chem. Soc. 1963, 993.
2. Kuck, D.; Grützmacher, H.-F. Adv. Mass Spectrom. 1980, 8, 867.
3. Kuck, D. Mass Spectrom. Rev. 1990, 9, 181; 583.
4. Kuck, D., to be published.
5. Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1964, 29, 123. Askani, R. In Houben-Weyl, 4th ed., Vol. 5/1b; Müller, E., Ed.; Thieme: Stuttgart, 1972; p 83 ff.
6. Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1964, 29, 123. Askani, R. In Houben-Weyl, 4th ed., Vol. 5/1b; Müller, E., Ed.; Thieme: Stuttgart, 1972; p 83 ff.
7. Kuck, D. Z. Naturforsch., Teil B 1984, 39, 369.
8. Baker, W.; McOmie, J. F. W.; Parfitt, S. D.; Watkins, D. A. M. J. Chem. Soc. 1957, 4026.
9. Smits, J. M. M.; Noordijk, J. H.; Beurskens, P. T.; Laarhoven, W. H.; Lijten, F.A.T. J. Cryst. Spectrosc. Res. 1986, 16, 23.
10. Barnes, R. A.; Beitchman, B. D. J. Am. Chem. Soc. 1954, 76, 5430.
11. Lamarche, J.-M.; Laude, B. Bull. Soc. Chim. France 1982, 97.
12. Chuen, C. C.; Fenton, S. W. J. Org. Chem. 1958, 23, 1538. Mittal, R. S. D.; Sethi, S. C.; Sukh Dev Tetrahedron 1973, 29, 1321.
13. Chuen, C. C.; Fenton, S. W. J. Org. Chem. 1958, 23, 1538. Mittal, R. S. D.; Sethi, S. C.; Sukh Dev Tetrahedron 1973, 29, 1321.
14. Truly classical triindane derivatives formed by dehydrative cyclocondensation are truxene and truxene quinone, known by now for more than a century: See, for example, Hausmann, J. Ber. Dtsch. Chem. Ges. 1889, 22, 2022. v. Kostanecki, S.; L. La̧czkowski Ber. Dtsch. Chem. Ges. 1897, 30, 2138. Wislicenus, W. Ber. Dtsch. Chem. Ges. 1898, 31, 2935.
15. Truly classical triindane derivatives formed by dehydrative cyclocondensation are truxene and truxene quinone, known by now for more than a century: See, for example, Hausmann, J. Ber. Dtsch. Chem. Ges. 1889, 22, 2022. v. Kostanecki, S.; L. La̧czkowski Ber. Dtsch. Chem. Ges. 1897, 30, 2138. Wislicenus, W. Ber. Dtsch. Chem. Ges. 1898, 31, 2935.
16. Truly classical triindane derivatives formed by dehydrative cyclocondensation are truxene and truxene quinone, known by now for more than a century: See, for example, Hausmann, J. Ber. Dtsch. Chem. Ges. 1889, 22, 2022. v. Kostanecki, S.; L. La̧czkowski Ber. Dtsch. Chem. Ges. 1897, 30, 2138. Wislicenus, W. Ber. Dtsch. Chem. Ges. 1898, 31, 2935.
17. Diederich, F.; Rubin, Y. Ang. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101, and work cited therein.
18. Diederich, F.; Rubin, Y. Ang. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101, and work cited therein.
19. Fabre, C.; Rassat, A. C. R. Acad. Sci. Paris Sér. 2 1989, 308, 1223.
20. Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920, and work cited therein. Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010. Borchardt, A.; Fuchicello, A.; Kilvay, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921.
21. Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920, and work cited therein. Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010. Borchardt, A.; Fuchicello, A.; Kilvay, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921.
22. Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920, and work cited therein. Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010. Borchardt, A.; Fuchicello, A.; Kilvay, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921.
23. The most prominent spherical polycyclic molecule with [5.5]-only anellation is pentagon dodecahedrane; see, for example: Olah, G. A., Ed., Cage Hydrocarbons; Wiley: New York, 1990.
24. Hoffmann, R. Scientific American 1993, 268 (2), 40.
25. Wudl, F. Acc. Chem. Res. 1992, 25, 157, and further articles in the March 1992 issue.
26. Hirsch, A. The Chemistry of the Fullerenes; Thieme: Stuttgart, 1994.
27. Curl, R. F.; Smalley, R. E. Science 1988, 242, 1017. Curl, R. F.; Smalley, R. E. Scientific American 1991, 265 (10), 32.
28. Curl, R. F.; Smalley, R. E. Science 1988, 242, 1017. Curl, R. F.; Smalley, R. E. Scientific American 1991, 265 (10), 32.
29. Kroto, H. W. Angew. Chem. 1992, 104, 113; Angew. Chem., Int. Ed. Engl. 1992, 31, 111.
30. Kroto, H. W. Angew. Chem. 1992, 104, 113; Angew. Chem., Int. Ed. Engl. 1992, 31, 111.
31. Kroto, H. W. Nature 1987, 329, 529. D'Arcy Thompson, W. On Growth and Form, 2nd ed., Vol. 2; Cambridge University Press: Cambridge, 1942; Ysel Press: Deventer, 1972; p. 732.
32. Kroto, H. W. Nature 1987, 329, 529. D'Arcy Thompson, W. On Growth and Form, 2nd ed., Vol. 2; Cambridge University Press: Cambridge, 1942; Ysel Press: Deventer, 1972; p. 732.
33. Woodward, R. B.; Fukunaga, T.; Kelly, R. C. J. Am. Chem. Soc. 1964, 86, 3162.
34. Deslongschamps, P.; Cheriyan, U. O.; Lambert, Y.; Mercier, J.-C.; Ruest, L.; Russo, R.; Soucy, P. Can. J. Chem. 1978, 56, 1687.
35. Paquette, L. A. Top. Curr. Chem. 1979, 79, 41. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry, Synthesis and Reactions; Springer: Berlin, 1987.
36. Paquette, L. A. Top. Curr. Chem. 1979, 79, 41. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry, Synthesis and Reactions; Springer: Berlin, 1987.
37. Paquette, L. A. Top. Curr. Chem. 1979, 79, 41. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry, Synthesis and Reactions; Springer: Berlin, 1987.
38. Monobenzotriquinacene: Paquette, L. A.; Kramer, J. D.; Lavrik, P. B.; Wyvratt, M. J. J. Org. Chem. 1977, 42, 503.
39. Thompson, H. W. Tetrahedron Lett. 1966, 6489.
40. Thompson, H. W. J. Org. Chem. 1968, 33, 621.
41. Ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1979, 44, 1508.
42. Ten Hoeve, W., Proefschrift (Doctoral thesis), Rijksuniversiteit te Groningen, 1979.
43. Langer, E.; Lehner, H. Tetrahedron 1973, 29, 375.
44. Neudeck, H.; Schlögl, K. Chem. Ber. 1977, 110, 2624.
45. Brewster, J. H.; Prudence, R.T.J. Am. Chem. Soc. 1973, 95, 1217.
46. Hill, R. K.; Cullison, D. A. J. Am. Chem. Soc. 1973, 95, 1229.
47. Gund, P.; Gund, T. M. J. Am. Chem. Soc. 1981, 103, 4458.
48. Agosta, W. C. in The Chemistry of Alkanes and Cycloalkanes; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1992, p. 927. Venepalli, B. R.; Agosta, W. C. Chem. Rev. 1987, 87, 399.
49. Agosta, W. C. in The Chemistry of Alkanes and Cycloalkanes; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1992, p. 927. Venepalli, B. R.; Agosta, W. C. Chem. Rev. 1987, 87, 399.
50. Fu, X.; Kubiak, G.; Zhang, W.; Han, W.; Gupta, A. K.; Cook, J. M. Tetrahedron 1993, 49, 1511.
51. Keese, R.; Luef, W. In Advances in Strain in Organic Chemistry, Vol. 3; Halton, B., Ed.; JAI Press: Greenwich, CT, 1993, p. 229. Keese R. In Organic Synthesis: Modern Trends; Chizhov, O., Ed.; Blackwell: Oxford, 1987; pp 43-52.
52. Keese, R.; Luef, W. In Advances in Strain in Organic Chemistry, Vol. 3; Halton, B., Ed.; JAI Press: Greenwich, CT, 1993, p. 229. Keese R. In Organic Synthesis: Modern Trends; Chizhov, O., Ed.; Blackwell: Oxford, 1987; pp 43-52.
53. Krohn, K. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U., Eds.; VCH: Weinheim, 1991; p. 371.
54. Simmons III, H. E., PhD Thesis, Harvard University, 1980.
55. Simmons III, H. E.; Maggio, J. E. Tetrahedron Lett. 1981, 22, 287.
56. Paquette, L. A.; Vazeux, M. Tetrahedron Lett. 1981, 22, 291.
57. Paquette, L. A.; Williams, R. V.; Vazeux, M.; Browne, A. R. J. Org. Chem. 1984, 49, 2194.
58. Paquette, L. A.; Snow, R. A.; Muthard, J. L.; Cynkowski, T. J. Am. Chem. Soc. 1978, 100, 1600.
59. Balaban, A. T. (Ed.), Chemical Applications of Graph Theory; Academic Press: London, 1976.
60. Walba, D. M. Tetrahedron 1985, 41, 3161.
61. Chambron, J.-C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131.
62. Liang, C.; Mislow, K. J. Math. Chem. 1994, 15, 245.
63. Bradsher, C. K. Chem. Rev. 1946, 38, 447.
64. Popp, F. D.; McEwen, W. E. Chem. Rev. 1958, 58, 321. Uhlig, F.; Snyder, H. R. Adv. Org. Chem. 1960, 1, 35.
65. Popp, F. D.; McEwen, W. E. Chem. Rev. 1958, 58, 321. Uhlig, F.; Snyder, H. R. Adv. Org. Chem. 1960, 1, 35.
66. Aubert, C.; Bégué, J.-P.; Bonnet-Delpon, D.; Mesureur, D. J. Chem. Soc., Perkin Trans. 1 1989, 395.
67. Bonnet-Delpon, D.; Cambillau, C.; Charpentier-Maurize, M.; Jacquot, R.; Mesureur, D.; Bégué, J.-P. J. Org. Chem. 1988, 53, 54.
68. Ginsburg, D. Propellanes: Structure and Reactions; Verlag Chemie: Weinheim, 1975.
69. Tobe, Y. In Cage Hydrocarbons, Chemistry and Applications; Ōsawa, E.; Yonemitsu, Ō., Eds.; VCH: New York, 1992; p 125.
70. Dyker, G.; Körning, J.; Jones, P. G.; Bubenitschek, P. Angew. Chem. 1993, 105, 1805; Angew. Chem., Int. Ed. Engl. 1993, 32, 1733.
71. Dyker, G.; Körning, J.; Jones, P. G.; Bubenitschek, P. Angew. Chem. 1993, 105, 1805; Angew. Chem., Int. Ed. Engl. 1993, 32, 1733.
72. Haag, R.; Fleischer, R.; Stahlke, D.; de Meijere, A. Angew. Chem. 1995, 107, 1642; Angew. Chem., Int. Ed. Engl. 1995, 34, 1492.
73. Haag, R.; Fleischer, R.; Stahlke, D.; de Meijere, A. Angew. Chem. 1995, 107, 1642; Angew. Chem., Int. Ed. Engl. 1995, 34, 1492.
74. Haag, R.; Ohlhorst, B.; Noltemeyer, M.; Fleischer, R.; Stahlke, D.; Schuster, A.; Kuck, D.; de Meijere, A. J. Am. Chem. Soc. 1995, 117, 10474.
75. Brunvoll, J.; Guidetti-Grept, R.; Hargittai, I.; Keese, R. Helv. Chim. Acta 1993, 76, 2838.
76. Kuck, D.; Schuster, A. Angew. Chem. 1988, 100, 1222; Angew. Chem., Int. Ed. Engl. 1988, 27, 1192.
77. Kuck, D.; Schuster, A. Angew. Chem. 1988, 100, 1222; Angew. Chem., Int. Ed. Engl. 1988, 27, 1192.
78. Kuck, D.; Paisdor, B.; Gestmann, D. Angew. Chem. 1994, 106, 1326; Angew. Chem., Int. Ed. Engl. 1994, 33, 1251.
79. Kuck, D.; Paisdor, B.; Gestmann, D. Angew. Chem. 1994, 106, 1326; Angew. Chem., Int. Ed. Engl. 1994, 33, 1251.
80. Kuck, D.; Schuster, A.; Paisdor, B.; Gestmann, D. J. Chem. Soc., Perkin Trans. 1 1995, 721.
81. Kuck, D.; Schuster, A.; Gestmann, D. J. Chem. Soc., Chem. Commun. 1994, 609.
82. Kuck, D.; Schuster, A.; Gestmann, D.; Posteher, F.; Pritzkow, H. Chemistry Eur. J. 1996, 2, 58.
83. Touron, P.; Laude, B. C. R. Acad. Sci., Sér. C 1979, 289, 53.
84. Schönberg, A.; Mamluk, M. Chem. Ber. 1973, 106, 849.
85. Schönberg, A.; Sidky, M. M. Chem. Ber. 1974, 107, 2341.
86. Kuck, D. Angew. Chem. 1984, 96, 515; Angew. Chem., Int. Ed. Engl. 1984, 23, 508.
87. Kuck, D. Angew. Chem. 1984, 96, 515; Angew. Chem., Int. Ed. Engl. 1984, 23, 508.
88. Kuck, D. Chem. Ber. 1994, 127, 409.
89. Kuck, D.; Bögge, H.; Müller, A., to be published.
90. Mosher, W. A.; Soeder, R. W. J. Org. Chem. 1971, 36, 1561.
91. de Winter, M. L.; Nauta, W. Th. Eur. J. Med. Chem., Chim. Thér. 1977, 12, 125.
92. Kuck, D.; Lindenthal, T.; Schuster, A. Chem. Ber. 1992, 125, 1449.
93. For similar cases of stereocontrolled complex-hydride reductions, see: de Vries, E. F. J.; Brussee, J.; van der Gen, A. J. Org. Chem. 1994, 59, 7133, and previous work cited therein.
94. Kuck, D.; Penk, M.; Bögge, H.; Müller, A., to be published.
95. Stevens, E. D.; Kramer, J. D.; Paquette, L. A. J. Org. Chem. 1976, 41, 2266.
96. Cawley, J. J.; Petrocine, D. V. J. Org. Chem. 1976, 41, 2608.
97. Cawley, J. J.; Petrocine, D. V. J. Org. Chem. 1975, 40, 1184.
98. Diol 41 was prepared by catalytic hydrogenation of the corresponding dione. For the reduction of other enolizable 1,3-diketones, see: Dumpis, T. T.; Vanags, G. Ya. Dokl. Akad. Nauk. SSSR 1962, 142, 42;
99. (b) ibid. 1962, 142, 132.
100. Sprague, J. M.; Adkins, H. J. Am. Chem. Soc. 1934, 56, 2669.
101. Harms, W. M.; Eisenbraun, E. J. Org. Prep. Proc. Int. 1971, 3, 239; Harms, W. M.; Eisenbraun, E. J. Org. Prep. Proc. Int. 1972, 4, 67.
102. Harms, W. M.; Eisenbraun, E. J. Org. Prep. Proc. Int. 1971, 3, 239; Harms, W. M.; Eisenbraun, E. J. Org. Prep. Proc. Int. 1972, 4, 67.
103. Kuck, D.; Siemeling, U., to be published.
104. Kuck, D.; Bögge, H. J. Am. Chem. Soc. 1986, 108, 8107.
105. Hoffmann, R.; Alder, R.; Wilcox, C. F. J. Am. Chem. Soc. 1970, 92, 4992.
106. Hoffmann, R. Pure Appl. Chem. 1971, 28, 181.
107. Lyons, J. E.; Rasmussen, D. R.; McGrath, M. P.; Nobes, R. H.; Radom, L. Angew. Chem. 1994, 106, 1722; Angew. Chem., Int. Ed. Engl. 1994, 33, 1667, and literature cited therein.
108. Lyons, J. E.; Rasmussen, D. R.; McGrath, M. P.; Nobes, R. H.; Radom, L. Angew. Chem. 1994, 106, 1722; Angew. Chem., Int. Ed. Engl. 1994, 33, 1667, and literature cited therein.
109. Erker, G.; Zwettler, R.; Krüger, C.; Noe, R.; Werner, S. J. Am. Chem. Soc. 1990, 112, 9620.
110. Ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1980, 45, 2925.
111. Ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1980, 45, 2930.
112. Shternberga, I. Ya.; Freimanis, Ya. F. Zh. Org. Khim. 1968, 4, 1081; J. Org. Chem. USSR 1968, 4, 1044.
113. Shternberga, I. Ya.; Freimanis, Ya. F. Zh. Org. Khim. 1968, 4, 1081; J. Org. Chem. USSR 1968, 4, 1044.
114. Popelis, Yu. Yu.; Pestunovich, V. A.; Shternberga, I. Ya.; Freimanis, Ya. F. Zh. Org. Khim. 1972, 8, 1860; J. Org. Chem. USSR 1972, 8, 1907.
115. Popelis, Yu. Yu.; Pestunovich, V. A.; Shternberga, I. Ya.; Freimanis, Ya. F. Zh. Org. Khim. 1972, 8, 1860; J. Org. Chem. USSR 1972, 8, 1907.
116. Kuck, D.; Schuster, A.; Krause, R. A. J. Org. Chem. 1991, 56, 3472.
117. Kuck, A.; Schuster, A.; Fusco, C.; Fiorentino, M.; Curci, R. J. Am. Chem. Soc. 1994, 116, 2375.
118. Curci, R.; Fusco, C.; Krause, R. A.; Barth, D.; Kuck, D., to be published.
119. Krause, R. A., Doctoral thesis, University of Bielefeld, 1992.
120. Seifert, M., Doctoral thesis, University of Bielefeld, 1991.
121. Kuck, D.; Eckrich, R.; Tellenbröker, J. J. Org. Chem. 1994, 59, 2511.
122. Grieco, P. A.; Brandes, E. B.; McCann, S.; Clark, J. D. J. Org. Chem. 1989, 54, 5849.
123. Keese, R. Angew. Chem. 1992, 104, 307, Angew. Chem., Int. Ed. Engl. 1992, 31, 344.
124. Keese, R. Angew. Chem. 1992, 104, 307, Angew. Chem., Int. Ed. Engl. 1992, 31, 344.
125. Luyten, M.; Keese, R. Tetrahedron 1986, 42, 1687.
126. Smit, W. A.; Buhanjuk, S. M.; Simonyan, S. O.; Shashkov, A. S.; Struchkov, Y. T.; Yanovsky, A. I.; Caple, R.; Gybin, A. S.; Anderson, L. G.; Whiteford, J. A. Tetrahedron Lett. 1991, 32, 2105.
127. Seifert, M.; Kuck, D., to be published.
128. Kubiak, G.; Fu, X.; Gupta, A. K.; Cook, J. M. Tetrahedron Lett. 1990, 31, 4285.
129. Kuck, D.; Seifert, M.; Dohmeier, S. Abstracts of Papers, 200th ACS National Meeting, Washington, D.C., 1990; ORGN 031.
130. For some hydrocarbons with extended, curved polycyclic framework, see: Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660. Pascal, R. A., Jr.; Ho, D. M. Tetrahedron Lett. 1992, 33, 13. Yamamoto, K.; Harada, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M.; Kai, Y.; Nakao, T.; Tanaka, M.; Harada, S.; Kasai, N. J. Am. Chem. Soc. 1988, 110, 3578. Yamamoto, K.; Saitho, Y.; Iwaki, D.; Ooka, T. Angew. Chem. 1991, 103, 1202; Angew. Chem., Int. Ed. Engl. 1992, 30, 1173.
131. For some hydrocarbons with extended, curved polycyclic framework, see: Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660. Pascal, R. A., Jr.; Ho, D. M. Tetrahedron Lett. 1992, 33, 13. Yamamoto, K.; Harada, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M.; Kai, Y.; Nakao, T.; Tanaka, M.; Harada, S.; Kasai, N. J. Am. Chem. Soc. 1988, 110, 3578. Yamamoto, K.; Saitho, Y.; Iwaki, D.; Ooka, T. Angew. Chem. 1991, 103, 1202; Angew. Chem., Int. Ed. Engl. 1992, 30, 1173.
132. For some hydrocarbons with extended, curved polycyclic framework, see: Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660. Pascal, R. A., Jr.; Ho, D. M. Tetrahedron Lett. 1992, 33, 13. Yamamoto, K.; Harada, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M.; Kai, Y.; Nakao, T.; Tanaka, M.; Harada, S.; Kasai, N. J. Am. Chem. Soc. 1988, 110, 3578. Yamamoto, K.; Saitho, Y.; Iwaki, D.; Ooka, T. Angew. Chem. 1991, 103, 1202; Angew. Chem., Int. Ed. Engl. 1992, 30, 1173.
133. For some hydrocarbons with extended, curved polycyclic framework, see: Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660. Pascal, R. A., Jr.; Ho, D. M. Tetrahedron Lett. 1992, 33, 13. Yamamoto, K.; Harada, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M.; Kai, Y.; Nakao, T.; Tanaka, M.; Harada, S.; Kasai, N. J. Am. Chem. Soc. 1988, 110, 3578. Yamamoto, K.; Saitho, Y.; Iwaki, D.; Ooka, T. Angew. Chem. 1991, 103, 1202; Angew. Chem., Int. Ed. Engl. 1992, 30, 1173.
134. For some hydrocarbons with extended, curved polycyclic framework, see: Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660. Pascal, R. A., Jr.; Ho, D. M. Tetrahedron Lett. 1992, 33, 13. Yamamoto, K.; Harada, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M.; Kai, Y.; Nakao, T.; Tanaka, M.; Harada, S.; Kasai, N. J. Am. Chem. Soc. 1988, 110, 3578. Yamamoto, K.; Saitho, Y.; Iwaki, D.; Ooka, T. Angew. Chem. 1991, 103, 1202; Angew. Chem., Int. Ed. Engl. 1992, 30, 1173.
135. Birch, A. J.; Smith, H. J. Chem. Soc. 1951, 1882.
136. Baschang, G.; Frei, J.; Morel, C.; Wacker, O. Ger. Offen. 2,033,959, 1971; Chem. Abstr. 1971, 74, 125269d.
137. Hagishita, S.; Kuriyama, K.; Hajashi, M.; Nakano, Y.; Shingu, K.; Nakgawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 496.
138. Kuck, D.; Paisdor, B.; Grützmacher, H.-F. Chem. Ber. 1987, 120, 589.
139. Paisdor, B.; Grützmacher, H.-F.; Kuck, D. Chem. Ber. 1988, 121, 1307.
140. Paisdor, B.; Kuck, D. J. Org. Chem. 1991, 56, 4753.
141. Kuck, D.; Hackfort, T. Abstracts of Papers, 8th International Symposium on Novel Aromatic Compounds (ISNA 8), Braunschweig, 1995; P 117.
142. Kuck, D.; Neumann, E.; Schuster, A. Chem. Ber. 1994, 127, 151.
143. Kuck, D.; Seifert, M. Chem. Ber. 1992, 125, 1461.
144. Allen, J. M.; Johnstone, K. M.; Shotter, R. G. Chem. Ind. (London) 1976, 108.
145. Nucleophile-induced cleavage reactions of 1,3-diketones have been encountered in polyquinane chemistry. See, for example: Han, W. C.; Takahashi, K.; Cook, J. M.; Weiss, U.; Silverton, J. V. J. Am. Chem. Soc. 1982, 104, 318; Venkatachalam, M.; Kubiak, G.; Cook, J. M.; Weiss, U. Tetrahedron Lett. 1985, 26, 4863.
146. Nucleophile-induced cleavage reactions of 1,3-diketones have been encountered in polyquinane chemistry. See, for example: Han, W. C.; Takahashi, K.; Cook, J. M.; Weiss, U.; Silverton, J. V. J. Am. Chem. Soc. 1982, 104, 318; Venkatachalam, M.; Kubiak, G.; Cook, J. M.; Weiss, U. Tetrahedron Lett. 1985, 26, 4863.