Molecules with Nonstandard Topological Properties: Centrohexaindane, Kuratowski's Cyclophane and Other Graph-theoretically Nonplanar Molecules

Strained Hydrocarbons: Beyond the van-t Hoff and Le Bel Hypothesis

Volumn , Issue , 2009, Pages 425-447

  Kuck, Dietmar ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Centrohexaindane; Graph theoretically nonplanar molecules; Kuratowski's cyclophane; Nonstandard topological properties

Indexed keywords

EID: 84889813286     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527627134.ch9     Document Type: Chapter

References (105)

1. J. H. Van't Hoff, Arch. Neerl. Sci. Exactes Nat. 1874, 9, 445-454;
2. J. A. Le Bel, Bull. Soc. Chim. Fr. 1874, 22, 337.
3. For symmetry and 'lesser symmetry', see: I. Hargittai, Ed., Fivefold Symmetry, World Scientific, Singapore, 1992;
4. E. Heilbronner, J. D. Dunitz, Reflections on Symmetry, VHCA, Basel and VCH, Weinheim, 1993.
5. R. W. Alder, P. R. Allen, D. Hnyk, D. W. H. Rankin, H. E. Robertson, B. A. Smart, R. J. Gillespie, I. Bytheway, J. Org. Chem. 1999, 64, 4226-4232.
6. S. Grilli, L. Lunazzi, A. Mazzanti, M. Pinamonti, J. E. Anderson, C. V. Ramana, P. S. Koranne, M. K. Gurjar, J. Org. Chem. 2002, 67, 6387-6394.
7. For a most recent review compounds containing carbon atoms with flattened or even planar coordination of four ligands, see: R. Keese, Chem. Rev. 2006, 106, 4787-4808.
8. F. Harary, in A. T. Balaban, Ed., Chemical Applications of Graph Theory, Academic Press, London, 1976, pp. 5-9.
9. J. Simon, in R. B. King, D. H. Rouvray, Eds., Graph Theory and Topology in Chemistry, Elsevier, Amsterdam, 1987, pp. 43-75.
10. D. M. Walba, Tetrahedron 1985, 41, 3161-3212.
11. D. Kuck, Liebigs Ann./Rec. 1997, 1043-1057.
12. C. Rücker, M. Mehringer, MATCH-Commun. Math. Comput. Chem. 2002, 41, 153-172.
13. J. P. Sauvage, Acc. Chem. Res. 1990, 23, 319-327.
14. C. Liang, K. Mislow, J. Math. Chem. 1994, 15, 245-260;
15. K. Mislow, Croat. Chem. Acta, 1996, 69, 485-511.
16. K. Mislow, in S. E. Denmark, Ed., Topics in Stereochemistry, Vol. 22, John Wiley & Sons, New York, 1999, pp. 1-82.
17. For the most recent overview on topology in chemistry, see: R. Herges, Chem. Rev. 2006, 106, 4820-4842.
18. J. Ristein in M. H. Nazare, A. J. Neves, Eds., Properties, Growth and Application of Diamond, Inspec, London, 2001, pp. 73-75.
19. A. Hirsch, M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim, 2005.
20. L. A. Paquette, Chem. Rev. 1989, 89, 1051-1065;
21. H. Prinzbach, K. Weber, Angew. Chem. Int. Ed. Engl. 1994, 33, 2239-2257.
22. Y. Sekine, M. Brown, V. Boekelheide, J. Am. Chem. Soc. 1979, 101, 3126-3127.
23. H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, Chapter 12.
24. See also: R. Gleiter, H. Hopf, Modern Cyclophane Chemistry, Wiley-VCH, Weinheim, 2004.
25. D. J. Cram, J. M. Cram, Container Molecules and Their Guests, Royal Society of Chemistry, Cambridge, 1994.
26. C. Thilgen, F. Diederich, Chem. Rev. 2006, 106, 5049-5135.
27. S. Yang, K. J. Taylor, M. J. Craycraft, J. Conceicao, C. L. Pettiette, O. Cheshnovsky, R. E. Smalley, Chem. Phys. Lett. 1988, 144, 431-436;
28. L. Adamowicz, J. Chem. Phys. 1991, 94, 1241-1246.
29. J. Szczepanski, R. Pellow, M. Vala, Z. Naturforsch. A 1992, 47, 595-604.
30. P. Gund, T. M. Gund, J. Am. Chem. Soc. 1981, 103, 4458-4465.
31. O. Ermer, Aspekte von Kraftfeld rech nungen, Wolfgang-Baur-Verlag, München, 1981; Section 4.6.3.
32. H. E. Simmons III, J. E. Maggio, Tetrahedron Lett. 1981, 22, 287-290;
33. J. E. Maggio, H. E. Simmons III, J. K. Kouba, J. Am. Chem. Soc. 1981, 103, 1579-1581;
34. S. A. Benner, J. E. Maggio, H. E. Simmons III, J. Am. Chem. Soc. 1981, 103, 1581-1582;
35. H. E. Simmons III, PhD Thesis, Harvard University, 1980.
36. L. A. Paquette, M. Vazeux, Tetrahedron Lett. 1981, 22, 291-294;
37. L. A. Paquette, R. V. Williams, M. Vazeux, A. R. Browne, J. Org. Chem. 1984, 49, 2194-2197.
38. D. Gestmann, H. Pritzkow, D. Kuck, Liebigs Ann. 1996, 1349-1359.
39. D. Kuck, Chem. Rev. 2006, 106, 4885-4925.
40. D. Kuck, Pure Appl. Chem. 2006, 78, 749-775.
41. C. Kuratowski, Fund. Math. 1930, 15, 271-283.
42. D. M. Walba, J. D. Armstrong, III, A. E. Perry, R. M. Richards, T. C. Homan, R. C. Haltiwanger, Tetrahedron 1986, 42, 1883-1894;
43. D. M. Walba, T. C. Homan, R. M. Richards, R. C. Haltiwanger, New J. Chem. 1993, 17, 661-681.
44. B. Mao, J. Am. Chem. Soc. 1989, 111, 6132-6136.
45. G. M. Crippen, J. Theor. Biol. 1974, 45, 327-338.
46. C. Liang, K. Mislow, J. Am. Chem. Soc. 1994, 116, 3588-3592;
47. C. Liang, K. Mislow, J. Am. Chem. Soc. 1995, 117, 4201-4213.
48. D. Kuck, A. Schuster, Angew. Chem. Int. Ed. Engl. 1988, 27, 1192-1194.
49. D. Kuck, B. Paisdor, D. Gestmann, Angew. Chem. Int. Ed. Engl. 1994, 33, 1251-1253
50. D. Kuck, A. Schuster, B. Paisdor, D. Gestmann, D. J. Chem. Soc., Perkin Trans. 1 1995, 721-732.
51. C. T. Chao, P. Gantzel, J. S. Siegel, K. K. Baldridge, R. B. English, D. M. Ho, Angew. Chem. Int. Ed. Engl. 1995, 34, 2657-2660.
52. D. M. Walba, R. M. Richards, R. C. Haltiwanger, J. Am. Chem. Soc. 1982, 104, 3219-3221.
53. T. Otsubo, F. Ogura, S. Misumi, Tetrahedron Lett. 1983, 24, 4851-4854;
54. T. Otsubo, Y. Aso, F. Ogura, S. Misumi, A. Kawamoto, J. Tanaka, Bull. Chem. Soc. Jpn. 1989, 62, 164-170.
55. J. P. Melder, R. Pinkos, H. Fritz, J. Wörth, H. Prinzbach, J. Am. Chem. Soc. 1992, 114, 10213-10231;
56. R. Pinkos, J. P. Melder, K. Weber, D. Hunkler, H. Prinzbach, J. Am. Chem. Soc. 1993, 115, 7173-7191.
57. M. Kamieth, F. G. Klärner, F. Diederich, Angew. Chem. Int. Ed. 1998, 37, 3303-3306;
58. F. G. Klärner, J. Panitzky, D. Preda, L. T. Scott, J. Mol. Modeling 2000, 6, 318-327.
59. D. Kuck, J. Tellenbröker, H. Bögge, J. Strübe, B. Neumann, H. G. Stammler, unpublished results.
60. Previous reviews on centropolyindane chemistry: (a) D. Kuck, in I. Hargittai, Ed., Quasicrystals, Networks, and Molecules of Fivefold Symmetry, VCH Publishers, New York 1990, Chapter 19;
61. D. Kuck, Synlett 1996, 949-965;
62. D. Kuck, Top. Curr. Chem. 1998, 196, 167-220.
63. D. Kuck, A. Schuster, D. Gestmann, J. Chem. Soc., Chem. Commun. 1994, 609-610;
64. D. Kuck, A. Schuster, D. Gestmann, F. Posteher, H. Pritzkow, Chem. Eur. J. 1996, 2, 58-67.
65. D. Kuck, H. Bögge, J. Am. Chem. Soc. 1986, 108, 8107-8109;
66. D. Kuck, Chem. Ber. 1994, 127, 409-425.
67. D. Kuck, M. Seifert, Chem. Ber. 1992, 125, 1461-1469.
68. D. Kuck, Angew. Chem. Int. Ed. Engl. 1984, 23, 508-509.
69. H. W. Thompson, Tetrahedron Lett. 1966, 6489-6494;
70. H. W. Thompson, J. Org. Chem. 1968, 33, 621-625.
71. B. Paisdor, D. Kuck, J. Org. Chem. 1991, 56, 4753-4759.
72. D. Kuck, T. Lindenthal, A. Schuster, Chem. Ber. 1992, 125, 1449-1460;
73. D. Kuck, E. Neumann, A. Schuster, Chem. Ber. 1994, 127, 151-164.
74. I. Ya. Shternberga, Ya. F. Freimanis, J. Org. Khim. USSR 1968, 4, 1044-1048.
75. W. Ten Hoeve, H. Wynberg, J. Org. Chem. 1979, 44, 1508-1514.
76. B. Bredenkötter, U. Flörke, D. Kuck, Chem. Eur. J. 2001, 7, 3387-3400.
77. M. S. Raasch, J. Org. Chem. 1980, 45, 856-867.
78. D. Kuck, A. Schuster, R. A. Krause, J. Org. Chem. 1991, 56, 3472-3475.
79. J. Tellenbröker, D. Kuck, Eur. J. Org. Chem. 2001, 1483-1489;
80. X. P. Cao, D. Barth, D. Kuck, Eur. J. Org. Chem. 2005, 3482-3488.
81. D. Kuck, in R. P. Thummel, Ed., Advances in Theoretically Interesting Molecules, Vol. 4, JAI Press, Greenwich, London, 1998, pp. 81-155.
82. J. Tellenbröker, D. Barth, D. Kuck, unpublished work.
83. D. Kuck, T. Hackfort, Polish J. Chem. 2007, 81, 875-892.
84. J. Tellenbröker, D. Barth, B. Neumann, H. G. Stammler, D. Kuck, Org. Biomol. Chem. 2005, 3, 570-571.
85. M. Harig, D. Kuck, Eur. J. Org. Chem. 2006, 1647-1655.
86. For the first syntheses of molecules bearing Möbius conjugated-electron systems, see D. Ajami, O. Oeckler, A. Simon, R. Herges, Nature 2003, 426, 819-821.
87. Note that, in contrast to their-electron system, the constitution of these hydrocarbons is topologically planar.
88. For related studies on Möbius-electron systems, see (a) C. Castro, Z. Chen, C. S. Wannere, H. Jiao, W. L. Karney, M. Mauksch, R. Puchta, N. J. R. van Eikema Hommes, P. von Rague Schleyer, J. Am. Chem. Soc. 2005, 127, 2425-2432;
89. H. S. Rzepa, Org. Lett. 2005, 7, 4637-4639.
90. J. E. P. Dahl, J. M. Moldowan, T. M. Peakman, J. C. Clardy, E. Lobkovsky, M. M. Olmstead, P. W. May, T. J. Davies, J. W. Steeds, K. E. Peters, A. Pepper, A. Ekuan, R. M. K. Carlson, Angew. Chem. Int. Ed. 2003, 42, 2040-2044.
91. A. T. Balaban, P. von Ragué Schleyer, Tetrahedron 1978, 34, 3599-3609.
92. W. Burns, M. A. McKervey, T. R. M. Michell, J. J. Rooney, J. Am. Chem. Soc. 1978, 100, 906-911;
93. M. A. McKervey, Chem. Soc. Rev. 1974, 3, 479-512;
94. M. A. McKervey, Tetrahedron 1980, 36, 971-992.
95. P. R. Schreiner, A. A. Fokin, O. Lauenstein, Y. Okamoto, T. Wakita, C. Rinderspacher, G. H. Robinson, J. K. Vohs, C. F. Campana, J. Am. Chem. Soc. 2002, 124, 13348-13349;
96. A. A. Fokin, B. A. Tkachenko, P. A. Gunchenko, D. V. Gusev, P. R. Schreiner, Chem. Eur. J. 2005, 11, 7091-7101;
97. P. R. Schreiner, N. A. Fokina, B. A. Tkachenko, H. Hausmann, M. Serafin, J. E. P. Dahl, S. Liu, R. M. K. Carlson, A. A. Fokin, J. Org. Chem. 2006, 71, 6709-6720;
98. A. A. Fokin, P. R. Schreiner, N. A. Fokina, B. A. Tkachenko, H. Hausmann, M. Serafin, J. E. P. Dahl, S. Liu, R. M. K. Carlson, J. Org. Chem. 2006, 71, 8532-8540.
99. Note that, in contrast to cyclohexamantane (36), the globular framework of [1(2,3)4]pentamantane ('Td-pentamantane', cf. ref. [68d]) is topologically planar.
100. T. Otsubo, S. Mizogami, I. Otsubo, Z. Tozuka, A. Sakagami, Y. Sakata, S. Misumi, Bull. Chem. Soc. Japan 1973, 46, 3519-3530;
101. T. Otsubo, H. Horita, S. Misumi, Synth. Commun. 1976, 6, 591-596.
102. M. Nakazaki, K. Yamamoto, S. Tanaka, H. Kametani, J. Org. Chem. 1977, 42, 287-291.
103. H. Dodziuk, K. S. Nowiski, Tetrahedron 1998, 54, 2917-2930.
104. C. J. F. Du, H. Hart, K. K. D. Ng, J. Org. Chem. 1986, 51, 3162-3165.
105. The structure of centrohexaindane (5) was used as 'The Graph of the Conference', 19th LL-Seminar on Graph Theory, Vienna, April 25-28, 2002. The author thanks Professor Dr. Peter F. Stadler (Leipzig, Germany) for kindly having communicated this to us.