Phenanthro[1.10]-annelated [3.3.3]propellanes by cyclodehydrogenation reactions of mono-, di-, and tribenzylidenetriptindanes

European Journal of Organic Chemistry

Volumn , Issue 11, 1999, Pages 2867-2878

  Hackfort, Thorsten ^a   Kuck, Dietmar ^a,b  

^a BIELEFELD UNIVERSITY   (Germany)

^b UNIVERSITY OF PADERBORN   (Germany)

Author keywords

Aromatic hydrocarbons; Cyclization; Cyclodehydrogenation; Phenanthrenes; Polycyclic hydrocarbons; Propellanes

Indexed keywords

AROMATIC HYDROCARBON; BENZYLIDENE DERIVATIVE; PHENANTHRENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

EID: 0032727924     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2867::aid-ejoc2867>3.0.co;2-b     Document Type: Article

References (73)

1. Reviews on propellanes: [1a] D. Ginsburg, Propellanes, Structure and Reactions; Verlag Chemie: Weinheim, 1975.
2. [1b] Y. Tobe, Propellanes. In: Carbocyclic Cage Compounds: Chemistry and Applications; (Eds.: E. Osawa, O. Yonemitsu); VCH Publishers: New York, 1992; pp 125-153.
3. [2a] A. Greenberg, J. L. Liebman, Strained Organic Molecules, Academic Press, New York, 1978.
4. [2b] F. Vögtle, Reizvolle Moleküle der Organischen Chemie, Teubner, Stuttgart, 1989.
5. [2c] H. Dodziuk, Modern Conformational Analysis, VCH, New York, 1995.
6. [2d] E. Osawa, O. Yonemitsu, Carbocyclic Cage Compounds, VCH, New York, 1992.
7. J. Tellenbröker, D. Kuck, Angew. Chem. 1999, 111, 1000-1004; Angew. Chem. Int. Ed. Engl. 1999, 38, 919-922, and literature cited therein.
8. J. Tellenbröker, D. Kuck, Angew. Chem. 1999, 111, 1000-1004; Angew. Chem. Int. Ed. Engl. 1999, 38, 919-922, and literature cited therein.
9. [4a] L. A. Paquette, A. M. Doherty, Polyquinane Chemistry, Synthesis and Reactions; Springer, Berlin, 1987.
10. [4b] L. A. Paquette, Top. Curr. Chem. 1979, 79, 41-165.
11. [4c] L. A. Paquette. Top. Curr. Chem. 1984, 119, 1-160.
12. [4d] B. M. Trost, Chem. Soc. Rev. 1982, 11, 141-170.
13. [4d] A. K Gupta, X. Fu, J. P Snyder, J. M. Cook, Tetrahedron 1991, 47, 3665-3710.
14. [4e] X. Fu, J. M. Cook. Aldrichimica Acta 1992, 25, 43-54.
15. [4f] G. Mehta, Chem. Rev. 1997, 97, 671-719.
16. [5a] H. W. Thompson, Tetrahedron Lett. 1966, 6489-6494.
17. [5b] H. W. Thompson, J. Org. Chem. 1968, 33, 621-625.
18. [6a] D. Kuck, B. Paisdor, H.-F. Grützmacher, Chem. Ber. 1987, 120, 589-595.
19. [6b] B. Paisdor, H.-F. Grützmacher, D. Kuck, Chem. Ber. 1988, 121, 1307-1313.
20. [6c] A. Ceccon, A. Gambaro, F. Manoli, A. Venzo, P. Ganis, G. Valle, D. Kuck, Chem. Ber. 1993, 126, 2053-2060.
21. D. Kuck, Synlett 1996, 949-965.
22. R. W. Alder, D. Colclough, F. Grams, A. G. Orpen, Tetrahedron 1990, 46, 7933-7940.
23. [9a] G. Dyker, J. Körning, P. Bubenitschek, P. G. Jones, Liebigs Ann. Recueil 1997, 203-209.
24. [9b] G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek, Angew. Chem. 1993, 105, 1805-1807; G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek Angew. Chem. Int. Ed. Engl. 1993, 32, 1733.
25. [9b] G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek, Angew. Chem. 1993, 105, 1805-1807; G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek Angew. Chem. Int. Ed. Engl. 1993, 32, 1733.
26. [10a] G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek, Tetrahedron 1996, 52, 14777-14786.
27. R. Crockett, G. Gescheidt, G. Dyker, J. Körning, Liebigs Ann. 1996, 1533-1539.
28. For a review, see: G. Dyker, J. Körning, F. Nerenz, P. Siemsen, S. Sostmann, A. Wiegand, P. G. Jones, P. Bubenitschek, Pure Appl. Chem. 1996, 68, 323-326.
29. B. Paisdor, D. Kuck, J. Org. Chem. 1991, 56, 4753-4759.
30. [13a] D. Kuck, B. Paisdor, D. Gestmann, Angew Chem. 1994, 106, 1326-1328; D. Kuck, B. Paisdor, D. Gestmann, Angew. Chem. Int. Ed. Engl. 1994, 33, 1251-1253.
31. [13a] D. Kuck, B. Paisdor, D. Gestmann, Angew Chem. 1994, 106, 1326-1328; D. Kuck, B. Paisdor, D. Gestmann, Angew. Chem. Int. Ed. Engl. 1994, 33, 1251-1253.
32. [13b] D. Kuck, A. Schuster, B. Paisdor, D. Gestmann, J. Chem. Soc., Perkin Trans. 1 1995, 721-732.
33. [13c] D. Gestmann, H. Pritzkow, D. Kuck, Liebigs Ann. 1996, 1349-1359.
34. 1H-NMR analysis of the mixture, two diasteromeric monobromoketones were formed in a ratio of ca. 1:1, as indicated by two singlets at = 5.66 and 5.94 (ArCHBr).
35. T. Hackfort, B. Neumann, H.-G. Stammler, D. Kuck, Eur. J. Org. Chem. 1999, 2879-2884.
36. For related stereospecific elimination processes, see: D. Kuck, E. Neumann, A. Schuster, Chem. Ber. 1994, 127, 151-164, and literature cited therein.
37. This one-proton singlet is almost isochronous with a two-proton triplet at δ = 7.12, but clearly resolved at 500 MHz (see ref. 21b).
38. [18a] V. J. Traynelis, W. L. Hergenrother, J. R. Livingston, J. A. Valicenti, J. Org. Chem. 1962, 27, 2377.
39. [18b] R Askani, Houben-Weyl, Methoden der Organischen Chemie, (Ed. E. Müller) 4th edn., Vol. 5/1b, Thieme, Stuttgart, 1972, pp 83-104.
40. [7] and literature cited therein.
41. B. Paisdor, Doctoral thesis, Universität Bielefeld, 1989.
42. [21a] T. Hackfort, B. Neumann, H.-G. Stammler, D. Kuck (to be published).
43. [21b] T. Hackfort, Doctoral thesis, Universität Bielefeld, 1997.
44. 9,10-Dibenzylidenetriptindan-11-one (Z,Z)-14 obtained by reacting mixtures of 11 and 12 (see Experimental Section) bears two cis-stilbene units, as revealed by single-crystal X-ray structure analysis: T. Hackfort, H. Pritzkow, D. Kuck (unpublished results, 1997).
45. D. Kuck, Liebigs Ann./Recueil 1997, 1043-1057.
46. D. Kuck, R. A. Krause, D. Gestmann, F. Posteher, A. Schuster, Tetrahedron 1998, 54, 5247-5258.
47. K. A Muszkat, Top. Curr. Chem. 1980, 88, 89-143.
48. H. Meier, Angew. Chem. 1992, 104, 1425-1446; H. Meier, Angew. Chem., Int. Ed. Engl. 1992, 31, 1399.
49. H. Meier, Angew. Chem. 1992, 104, 1425-1446; H. Meier, Angew. Chem., Int. Ed. Engl. 1992, 31, 1399.
50. [27a] C. S. Wood, F. B. Mallory, J. Org. Chem. 1964, 29, 3373-3377.
51. [27b] F. B. Mallory, C. S. Wood, J. T. Gordon, J. Am. Chem. Soc. 1964, 86, 3094-3102.
52. [27c] H Meier, Houben-Weyl, Methoden der organischen Chemie, (Ed: E. Müller) 4th. Edn, Vol. IV/5a, Thieme, Stuttgart, 1975, pp 511-538.
53. L. Liu, B. Yang, T. J. Katz, M. K. Poindexter, J. Org. Chem. 1991, 56, 3769-3775.
54. [5b,6c]) and ca. 0.47 ppm upfield from those of 19 (δ = 4.08, see text).
55. [30a] L. A. Paquette, C. C. Liao, R. L. Burson, R. E. Wingard Jr., C. N. Shih, J. Fayos, J. Clardy, J. Am. Chem. Soc. 1977, 99, 6935-6945.
56. [30b] L. A. Paquette, T. G. Wallis, T. Kempe, G. G. Christoph, J. P. Springer, J. Clardy, J. Am. Chem. Soc. 1977, 99, 6946-6954.
57. [30c] L. A Paquette, R. E. Wingard, Jr., R. K. Russell, J. Am. Chem. Soc. 1972, 94, 4739-4741.
58. [30d] L. A Paquette, Angew. Chem. 1978, 90, 114-125; L. A Paquette, Angew. Chem., Int. Ed. Engl. 1978, 17, 106.
59. [30d] L. A Paquette, Angew. Chem. 1978, 90, 114-125; L. A Paquette, Angew. Chem., Int. Ed. Engl. 1978, 17, 106.
60. [31a] E. Vogel, U. H. Brinker, K. Nachtkamp, J. Wassen, K. Müllen, Angew. Chem. 1973, 85, 760-762; E. Vogel, U. H. Brinker, K. Nachtkamp, J. Wassen, K. Müllen, Angew. Chem., Int. Ed. Engl. 1973, 12, 658.
61. [31a] E. Vogel, U. H. Brinker, K. Nachtkamp, J. Wassen, K. Müllen, Angew. Chem. 1973, 85, 760-762; E. Vogel, U. H. Brinker, K. Nachtkamp, J. Wassen, K. Müllen, Angew. Chem., Int. Ed. Engl. 1973, 12, 658.
62. [31b] H. Günter, H. Schmickler, U. H. Brinker, K. Nachtkamp, J. Wassen, E. Vogel, Angew. Chem. 1973, 85, 762-763; H. Günter, H. Schmickler, U. H. Brinker, K. Nachtkamp, J. Wassen, E. Vogel, Angew. Chem., Int. Ed. Engl. 1973, 12, 660.
63. [31b] H. Günter, H. Schmickler, U. H. Brinker, K. Nachtkamp, J. Wassen, E. Vogel, Angew. Chem. 1973, 85, 762-763; H. Günter, H. Schmickler, U. H. Brinker, K. Nachtkamp, J. Wassen, E. Vogel, Angew. Chem., Int. Ed. Engl. 1973, 12, 660.
64. R. V. Williams, H. A. Kurtz, B. Farley, Tetrahedron 1988, 44, 7455-7460.
65. T. Kawano, C. Ikemoto, I. Ueda, Tetrahedron Lett. 1998, 39, 6491-6494.
66. [34a] D. bosse, A. de Meijere, Angew. Chem. 1974, 86, 706-707; D. Bosse, A. de Meijere, Angew. Chem., Int. Ed. Engl. 1974, 13, 663.
67. [34a] D. bosse, A. de Meijere, Angew. Chem. 1974, 86, 706-707; D. Bosse, A. de Meijere, Angew. Chem., Int. Ed. Engl. 1974, 13, 663.
68. [34b] Firma Otto Fritz GmbH (NORMAG), Hofheim/ Taunus, Germany.
69. [35a] G. S. Hammond, J. Saltiel, A. A Lamola, N. J. Turro, J. S Bradshaw, D. O Cowan, R. C Counsell, V. Vogt, Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197-3217.
70. [35b] F. B Mallory, C. S. Wood, J. T Gordon, L. C Lindquist, M. L Savitz, J. Am. Chem. Soc. 1962, 84, 4361-4362.
71. K. Wimmer, Hauben-Weyl: Methoden der Organischen Chemie, (Ed: E. Müller) 4th Edn.; Vol. IV/2; Thieme, Stuttgart, 1955; pp 192-205.
72. [37a] L. A. Paquette, Y. Miyahara, C. W Doecke, J. Am. Chem. Soc. 1986, 110, 1716-1718.
73. [37b] L. A. Paquette, Y. Miyahara, J. Org. Chem. 1987, 52, 1265-1272.