Helical transition-metal compounds: Preorganisation of the ligands by a paracyclophane group

Chemical Communications

Volumn , Issue 16, 1996, Pages 1885-1886

  Comba, Peter ^a   Fath, Andreas ^a   Huttner, Gottfried ^a   Zsolnai, Laszlo ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001876531     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001885     Document Type: Article

References (35)

1. E. C. Constable, Nature, 1990, 346, 314; J. P. Sauvage, Acc. Chem. Res., 1990, 23, 319; J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304; E. C. Constable, Chem. Ind., (London), 1994, 56.
2. E. C. Constable, Nature, 1990, 346, 314; J. P. Sauvage, Acc. Chem. Res., 1990, 23, 319; J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304; E. C. Constable, Chem. Ind., (London), 1994, 56.
3. E. C. Constable, Nature, 1990, 346, 314; J. P. Sauvage, Acc. Chem. Res., 1990, 23, 319; J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304; E. C. Constable, Chem. Ind., (London), 1994, 56.
4. E. C. Constable, Nature, 1990, 346, 314; J. P. Sauvage, Acc. Chem. Res., 1990, 23, 319; J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304; E. C. Constable, Chem. Ind., (London), 1994, 56.
5. E. C. Constable, Nature, 1990, 346, 314; J. P. Sauvage, Acc. Chem. Res., 1990, 23, 319; J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304; E. C. Constable, Chem. Ind., (London), 1994, 56.
6. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
7. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
8. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
9. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
10. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
11. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
12. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
13. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
14. U. Koert, M. M. Harding and J.-M. Lehn, Nature, 1990, 346, 339; W. Zarges, J. Hall and J.-M. Lehn, Helv. Chim. Acta, 1991, 74, 1843; J. K. Judice, S. J. Keipert and D. J. Cram, J. Chem. Soc., Chem. Commun., 1993, 1323; K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruna and C. Arana, Inorg. Chem., 1993, 32, 4436; R. Krämer, J.-M. Lehn, A. De Cian and J. Fischer, Angew. Chem., 1993, 105, 764; Angew. Chem., Int. Ed. Engl., 1993, 32, 703; E. C. Constable, A. J. Edwards, P. R. Raithby and J. V. Walker, Angew. Chem., 1993, 105, 1486; Angew. Chem., Int. Ed. Engl., 1993, 32, 1465; A. Bilyk and M. M. Harding, J. Chem. Soc., Dalton Trans., 1994, 77.
15. P. Comba, A. Fath, T. W. Hambley and D. T Richens, Angew. Chem., Int. Ed. Engl., 1995, 34, 1883.
16. F. J. Schmitz, M. B. Ksebati, J. S. Cheng, J. L. Wang, M. B. Hossain, D. van der Helm, M. H. Engel, A. Serban and J. A. Silfer, J. Org. Chem., 1989, 54, 3463; J. P. Michael and G. Pattenden, Angew. Chem., 1993, 105, 1; Angew. Chem., Int. Ed. Engl., 1993, 1.
17. F. J. Schmitz, M. B. Ksebati, J. S. Cheng, J. L. Wang, M. B. Hossain, D. van der Helm, M. H. Engel, A. Serban and J. A. Silfer, J. Org. Chem., 1989, 54, 3463; J. P. Michael and G. Pattenden, Angew. Chem., 1993, 105, 1; Angew. Chem., Int. Ed. Engl., 1993, 1.
18. F. J. Schmitz, M. B. Ksebati, J. S. Cheng, J. L. Wang, M. B. Hossain, D. van der Helm, M. H. Engel, A. Serban and J. A. Silfer, J. Org. Chem., 1989, 54, 3463; J. P. Michael and G. Pattenden, Angew. Chem., 1993, 105, 1; Angew. Chem., Int. Ed. Engl., 1993, 1.
19. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
20. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
21. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
22. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
23. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
24. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
25. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
26. W. H. Laarhoven and R. G. M. Veldhurs, Tetrahedron Lett, 1972, 1823; E. M. Kosower, H. Dodink, B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1977, 31, 526; B. Thulin and O. Wennerström, Acta Chem. Scand. Ser. B, 1976, 30, 688; D. N. Leach and H. A. Reiss, J. Org. Chem., 1978, 43, 2484; B. Thulin and O. Wennerström, Tetrahedron Lett., 1977, 929; M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1977, 96, 7380; R. C. Helgeson, J. M. Timko and D. J. Cram, J. Am. Chem. Soc., 1974, 99, 6411.
27. P. Comba, A. Fath, T. W. Hambley and A. Vielfort, submitted for publication.
28. (a) D. J. Cram, T. Kaneda, R. C. Helgeson and G. M. Lein, J. Chem. Soc., Chem. Commun., 1979, 948;
29. (b) D. J. Cram and G. M. Lein, J. Am. Chem. Soc., 1985, 107, 3657;
30. (c) P. Comba, A. Fath, A. Kühner and B. Nuber, submitted for publication.
31. (a) S. R. Cooper, in Crown Compounds Toward Future Applications, ed. S. R. Cooper, VCH, Weinheim, 1992, p. 112;
32. (b) R. Menif and A. E. Martell, J. Chem. Soc., Chem. Commun., 1989, 1521;
33. (c) P. Comba, T. W. Hambley, P. Hilfenhaus and D. T. Richens, J. Chem. Soc., Dalton Trans., 1996, 553.
34. G. M. Sheldrick, SHELX93, A Program for Crystal Structure Refinement, University of Göttingen, 1993.
35. G. M. Sheldrick, SHELX86, A Program for Crystal Structure Refinement, University of Göttingen, 1986.