Synthesis of sterically rigid macrocycles by the use of pressure-induced repetitive Diels-Alder reactions

Liebigs Annales

Volumn , Issue 3, 1997, Pages 501-516

  Benkhoff, Johannes ^a   Boese, Roland ^a   Klärner, Frank Gerrit ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Bis dienes; Bis dienophiles; Cycloadditions; endo,exo Stereoselectivity; High pressure chemistry; Macrocycles; Repetitive Diels Alder reactions

Indexed keywords

EID: 19944362262     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970310     Document Type: Article

References (76)

1. Part of these results have been reported in a communication. J. Benkhoff, R. Boese, F.-G. Klärner, A. E. Wigger, Tetrahedron Lett. 1994, 35, 73-76.
2. [2a] Monographs: F. Vögtle, Supramolekulare Chemie, Teubner, Stuttgart, 1989.
3. F. Diederich, Cyclophanes, The Royal Society of Chemistry, Cambridge, 1994.
4. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
5. Examples: [2b] B. R. Peterson, P. Wallimann, D. R. Carcanages, F. Diederich, Tetrahedron 1995, 51, 401-421;
6. B. R. Peterson, F. Diederich, Angew. Chem. 1994, 106, 1688-1690;
7. Angew. Chem. Int. Ed. Engl. 1994, 33, 1625-1628.
8. [2c] G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139-11140.
9. [2d] J. Rebek, Jr., Acc. Chem. Res. 1990, 23, 399-404;
10. M. M. Conn, G. Deslongchamps, J. de Mendoza, J. Rebek, Jr., J. Am. Chem. Soc. 1993, 115, 3548-3557.
11. [2e] S. S. Yoon, W. C. Still, J. Am. Chem. Soc. ibid. 1993, 115, 823-834.
12. [2f] D. M. Perreault, X. H. Chen, E. V. Anslyn, Tetrahedron 1995, 51, 353-362;
13. C. Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
14. [2g] R. P. Bonarlaw, J. K. M. Sanders, J. Am. Chem. Soc. ibid. 1995, 117, 259-271.
15. [2h] G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, 2nd Ed. Springer, Berlin, 1994.
16. [2i] T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395.
17. AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
18. PM3: J. J. P. Stewart, J., Computational Chem. 1989, 10, 209. The AM1 or PM3 calculations were performed by the use of SPARTAN 3.2. SPARTAN 3.2 distributed by W. J. Hehre, Department of Chemistry, University of California, Irvine, California 92717 and L. D. Burke, Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, California, 92715.
19. [4a] E. G. Cox, D. W. J. Cruikshank, J. A. C. Smith, Proc. R. Soc. London 1958, A247, 1-21;
20. K. C. Janda, J. C. Hemminger, J. S. Winn, S. Novick, S. J. Harris, W. Klemperer, J. Chem. Phys. 1975, 63, 1419;
21. C. Krieger, F. Diederich, Chem. Ber. 1985, 118, 3620-3631;
22. [4b] S. K. Burley, G. A. Petsko, Science 1985, 229, 23;
23. J. Am. Chem. Soc. 1986, 108, 7995-8001 .
24. [4c] J. Singh, J. M. Thornton, FEBS Lett. 1985, 191, 1-6;
25. J. Mol. Biol. 1990, 211, 595-614.
26. [4d] I. Peterson, T. Liljefors, J. Comput. Chem. 1987, 8, 1139-1145;
27. N. L. Allinger, J.-H. Lu, J. Comput. Chem. 1987, 8, 1146-1153;
28. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 772, 5525-5534;
29. C. A. Hunter, Chem. Soc. Rev. 1994, 101-109.
30. [4c] W. L. Jorgensen, D. L. J. Serverance, J. Am. Chem. Soc. 1990, 112, 4768-4774;
31. [4f] G. Karlström, P. Linse, A. Wallquist, B. Jönsson, J. Am. Chem. Soc. 1983, 105, 3777-3782;
32. P. Hobza, H. L. Selzle, E. W. Schlag, J. Am. Chem. Soc. 1994, 116, 3500-3506.
33. [4g] L. F. Newcomb, T. S. Haque, S. H. Gellmann, J. Am. Chem. Soc. 1995, 117, 6509-6519;
34. H. S. Paliwal, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497-4498.
35. F. H. Kohnke, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Angew. Chem., 1987, 99, 941-943;
36. Angew. Chem. Int. Ed. Engl. 1987, 26, 892-894;
37. P. R. Ashton, G. R. Brown, N. S. Isaacs, D. Guiffrida, F. H. Kohnke, J. P. Mathias, A. M. Z. Slawin, D. R. Smith, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc., 1992, 114, 6330-6353;
38. J. P. Mathias, J. F. Stoddart, Chem. Soc. Rev. 1992, 21, 215-225;
39. P. R. Ashton, U. Girreser, D. Giuffrida, F. H. Kohnke, J. P. Mathias, F. M. Raymo, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc., 1993, 115, 5422-5429;
40. P. R. Ashton, J. P. Mathias, J. F. Stoddart, Synthesis 1993, 221-224.
41. H. Hart, C. Lai, G. C. Nwokoyu, S. Shamonilian, Tetrahedron 1987, 5203-5224 and cited literature.
42. [7a] W. Albrecht, Justus Liebigs Ann. Chem. 1906, 348, 31-49.
43. [7b] J. Meinwald G. A. Wiley, J. Am. Chem. Soc. 1958, 80, 3667-3671.
44. [7c] R. C. Cookson, E. Grundwell, J. Hudec, Chem. Ind. (London) 1958, 1003-1004;
45. R. C. Cookson, R. R. Hill, J. Hudec, J. Chem. Soc. 1964, 3043-3062;
46. R. C. Cookson, R. Grundwell, J. Hudec, J. Chem. Soc. A64, 3062.
47. [7d] D. Butler, R. Smits, D. A. Evans, K. D. V. Weerasuria, R. N. Warrener, Tetrahedron Lett. 1996, 37, 2157-2160.
48. Starting from exo-14 the Diels-Alder reaction with 1,3-cyclopentadiene is expected to produce the adduct exo,trans,endo-15 which has the desired syn-configuration of the two methylene bridges. But we were not able to reproduce the synthesis of exo-14 reported by B. Pandey, P. V. Dalvi, A. A. Athawale, B. G. Pant, P. P. Kewale, J. Chem. Soc., Chem. Commun. 1990, 1505-1506;
49. B. Pan-dey, P. V. Dalvi, Angew. Chem. 1993, 105, 1724-1726;
50. Angew. Chem. Int. Ed. Engl. 1993, 32, 1612-1614.
51. M. Kamieth, F.-G. Klärner unpublished results.
52. G. Mehta, S. Padina, S. R. Karra, J. Org. Chem. 1989, 54, 1342-1346;
53. G. Mehta, S. Padina, V. Tappabhi, A. Pramanik, J. Chandrasekhar, J. Am. Chem. Soc. 1990, 112, 2942-2949;
54. G. Metha, S. Padina, Tetrahedron 1991, 37, 7807-7820.
55. K. Alder, S. Hartung, O. Netz, Chem. Ber. 1957, 90, 1-7;
56. M. A. Bowe, R. G. J. Miller, J. B. Rose, D. G. M. Wood, J. Chem. Soc. 1960, 1541-1547;
57. T. Toda, T. Ohya, T. Mukai, Bull. Chem. Soc. Jpn. 1912, 45, 1561-1562.
58. The stereochemistry of the Diels-Alder reaction between p-benzoquinone and bis-exo-ethylidenenorbornene was analyzed by L. A. Paquette, A. G. Schaefer, J. F. Blount, J. Am. Chem. Soc. 1983, 105, 3642-3649.
59. A review and discussion of exo- und endo-addition of norbornene and norborenene derivatives:
60. [13a] R. Gleiter, M. C. Böhm, Pure Appl. Chem. 1983, 55, 237-244.
61. [13b] F. K. Brown, K. N. Houk, J. Am. Chem. Soc. 1985, 107, 1971-1978.
62. [13c] C. G. Wipff, K. Morokuma, Tetrahedron Lett. 1980, 21, 4445-4449.
63. [13d] K. N. Houk, M. N. Paddon-Row, P. Caramella, N. G. J. Rondau, J. Am. Chem. Soc. 1981, 103, 2436-2440.
64. Florey, P. Vogel, Helv. Chim. Acta 1975, 58, 1488-1492;
65. O. Pilet, P. Vogel, Helv. Chim. Acta 1981, 64, 2563-2570.
66. P. v. R. Schleyer, J. Am. Chem. Soc. 1967, 29, 701-703;
67. J. Am. Chem. Soc. ibid. 3901-3903;
68. K. N. Houk, in Reactive Intermediates (Ed. M. Jones, Jr., R. A. Moss), Vol. 1, Wiley, New York 1978, p. 326;
69. S. Inagaki, H. Fugimoto, K. Fukui, J. Am. Chem. Soc. 1978, 98, 4054-4061;
70. R. Huisgen, Pure Appl. Chem. 1981, 53, 171-187;
71. K. N. Houk, N. G. Rondau, F. K. Brown, W. L. Jorgensen, J. D. Madura, D. C. Spellmeyer, J. Am. Chem. Soc. 1983, 105, 5980-5988;
72. O. Ermer, P. Bell, S. A. Mason, Angew. Chem. 1989, 101, 129S-1231.
73. F.-G. Klärner, J. Benkhoff, R. Boese, U. Burkert, M. Kamieth, U. Naatz, Angew. Chem. 1996, 108, 1195-1198;
74. Angew. Chem. Int. Ed. Engl. 1996, 35, 1130-1133.
75. High-pressure equipment (up to 14 kbar): A. W. Birks, Department of Mechanical and Industrial Engineering at the Queen's University of Belfast; A. Hofer, Mülheim, Ruhr.
76. Further details of the X-ray crystal structure determination can be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-406074 (1a), CSD-406075 (endo, syn-25), and CSD-406076 (endo, trans, endo-22), the names of the authors and the journal citation.