Synthesis and structural peculiarities of homeomorphic phosphorus bridgehead macrobicyclic compounds and novel dioxaphospha[3.1.1.]p,m,p-cyclophanes

Chemistry - A European Journal

Volumn 8, Issue 24, 2002, Pages 5622-5629

  Bauer, Ingmar ^a   Fröhlich, Roland ^b   Ziganshina, Albina Yu ^c   Prosvirkin, Alexander V ^c   Gruner, Margit ^a   Kazakova, Ella Kh ^c   Habicher, Wolf D ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

Cage compounds; Cyclophanes; Isomers; Phosphates; Structure elucidation

Indexed keywords

ISOMERS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

STRUCTURAL PECULIARITIES;

PHOSPHORUS COMPOUNDS;

CYCLOPHANE DERIVATIVE; PHOSPHATE; PHOSPHORUS;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CYCLIZATION; ISOMER; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0346666963     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021216)8:24<5622::AID-CHEM5622>3.0.CO;2-P     Document Type: Article

References (60)

1. Reviewed in: A. M. Caminade, J. P. Majoral, Chem. Rev. 1994, 94, 1183-1213.
2. For example monographs: a) N. Krause, Metallorganische Chemie, Spektrum, Heidelberg, 1996;
3. b) M. Schlosser, Organometallics in Synthesis, Wiley, Chichester, 1996;
4. c) L. Brandsma, S. F. Vasilevsky H. D. Verkruijsse, Application of Transition Metal Catalyst in Organic Synthesis, Springer, Berlin, 1997;
5. d) E. C. Constable, Metals and Ligand Reactivity: An Introduction to the Organic Chemistry of Metal Complexes, Wiley-VCH, Weinheim, 1996.
6. a) I. S. Antipin, I. I. Stoikov, E. M. Pinkhassik, N. A. Fitseva, I. Stibor, A. I. Konovalov, Tetrahedron Lett. 1997, 38, 5865-5868;
7. b) Metal complexation with P-containing macrocycles reviewed in: G. G. Talanova, Ind. Eng. Chem. Res. 2000, 39, 3550-3565.
8. a) J. E. Parks, B. E. Wagner, R. H. Holm, J. Am. Chem. Soc. 1970, 92, 3500-3502;
9. a) M. R. Churchill, A. H. Reis, J. Chem. Soc. Chem. Commun. 1970, 879-880.
10. b) A. Höhn, R. J. Geue, A. M. Sargeson, A. C. Willis, J. Chem. Soc. Chem. Commun. 1989, 1644-1645.
11. C. Bolm, K. B. Sharpless, Tetrahedron Lett. 1988, 29, 5101-5104.
12. a) B. P. Friedrichsen, H. W. Whitlock, J. Am. Chem. Soc. 1989, 111, 9132-9134;
13. b) B. P. Friedrichsen, R. P. Powell, H. W. Whitlock, J. Am. Chem. Soc. 1990, 112, 8931-8941.
14. a) A. A. Chaikovskaya, T. N. Kudrya, R. I. Yurchenko, O. M. Voitse-khovskaya, A. M. Pinchuk, Zh. Obshch. Khim. 1988, 58, 1925;
15. b) T. N. Koodrja, A. S. Stepanek, R. I. Yurchenko, A. A. Tschaikovskaja, S. E. Lavrova, Phosphorus Sulfur Silicon Relat. Elem. 1990, 51, 384-385.
16. a) F. Gonce, A. M. Caminade, F. Boutonnet, J. P. Majoral, J. Org. Chem. 1992, 57, 970-975;
17. b) J. Mitjaville, A. M. Caminade, R. Mathieu, J. P. Majoral, J. Am. Chem. Soc. 1994, 116, 5007-5008;
18. c) J. Mitjaville, A. M. Caminade, J. P. Majoral, J. Chem. Soc. Chem. Commun. 1994, 2161-2162;
19. d) A. M. Caminade, J. P. Majoral, Synlett 1996, 1019-1028.
20. Ch. B. Allan, L. O. Spreer, J. Org. Chem. 1994, 59, 7695-7700.
21. S. F. E. Houssamy, Egypt. J. Chem. 1998, 41, 155-174.
22. a) S. Dell, N. J. Vogelaar, D. M. Ho, R. A. Pascal, Jr., J. Am. Chem. Soc. 1998, 120, 6421-6422;
23. b) Y. T. Chen, K. K. Baldridge, D. M. Ho, R. A. Pascal, Jr., J. Am. Chem. Soc. 1999, 121, 12082-12087;
24. c) S. Dell, D. M. Ho, R. A. Pascal, Jr., J. Org. Chem. 1999, 64, 5626-5633.
25. a) I. Bauer, W. D. Habicher, Phosphorus Sulfur Silicon Relat. Elem. 1997, 130, 89-105;
26. b) I. Bauer, W. D. Habicher, Phosphorus Sulfur Silicon Relat. Elem. 1999, 147, 23-24;
27. c) I. Bauer, O. Rademacher, M. Gruner, W. D. Habicher, Chem. Eur. J. 2000, 6, 3043-3051; in this paper the term "tripod-capping" was used for the reaction of two molecules PCl3 with three molecules diphenol to form macrobicyclic compounds. This approach is better described as a "double-capping" method as one molecule PCl3 contributes only one atom to the macrobicyclic product (B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry, VCH, Weinheim, New York, Basel, Cambridge, 1992, p. 242.
28. c) I. Bauer, O. Rademacher, M. Gruner, W. D. Habicher, Chem. Eur. J. 2000, 6, 3043-3051; in this paper the term "tripod-capping" was used for the reaction of two molecules PCl3 with three molecules diphenol to form macrobicyclic compounds. This approach is better described as a "double-capping" method as one molecule PCl3 contributes only one atom to the macrobicyclic product (B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry, VCH, Weinheim, New York, Basel, Cambridge, 1992, p. 242.
29. V.P. Rudavskii, D. M. Zavalishina, E. I. Smirnova, N. V. Kofanova, Farm. Zh. (Kiev) 1975, 30, 47.
30. S. B. Wild, Pure Appl. Chem. 1990, 62, 1139-1144.
31. a) R. A. Pascal, Jr., A. P. West, Jr., D. Van Engen, J. Am. Chem. Soc. 1990, 112, 6406-6407;
32. b) R. P. L'Esperance, A. P. West, Jr., D. Van Engen, R. A. Pascal, Jr., J. Am. Chem. Soc. 1991, 113, 2672-2676;
33. c) A. P. West, N. Smyth, C. M. Kraml, D. M. Ho, R. A. Pascal, Jr., J. Org. Chem. 1993, 58, 3502-3506.
34. a) R. W. Alder, C. Ganter, C. J. Harris, A. G. Orpen, Phosphorus Sulfur Silicon Relat. Elem. 1993, 77, 234-235;
35. b) R. W. Alder, D. D. Ellis, R. Gleiter, Ch. J. Harris, H. Lange, A. G. Orpen, D. Read, P. N. Taylor, J. Chem. Soc. Perkin Trans. 1, 1998, 1657-1668;
36. c) R. Alder, D. Read, Angew. Chem. 2000, 112, 3001-3004; Angew. Chem. Int. Ed. 2000, 39, 2879-2882;
37. c) R. Alder, D. Read, Angew. Chem. 2000, 112, 3001-3004; Angew. Chem. Int. Ed. 2000, 39, 2879-2882;
38. d) R. W. Alder, C. P. Butts, A. G. Orpen, D. Read, J. Chem. Soc. Perkin Trans. 2, 2001, 288-295;
39. e) R. W. Alder, C. P. Butts, A. G. Orpen, D. Read, J. M. Oliva, J. Chem. Soc. Perkin Trans. 2, 2001, 282-287;
40. f) D. E. Berning, K. V. Katti, Ch. L. Barnes, W. A. Volkert, J. Am. Chem. Soc. 1999, 121, 1658-1664.
41. a) F. Vögtle, Cyclophan-Chemie, Teubner, Stuttgart, 1990;
42. b) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry, VCH, Weinheim, New York, Basel, Cambridge, 1993;
43. c) review in: R. W. Alder, S. P. East, Chem. Rev. 1996, 96, 2097-2111;
44. d) F. Vögtle, Supramolekulare Chemie, Teubner, Stuttgart, 1992;
45. e) F. Diederich, Monographs in Supramolecular Chemistry, No.2 Cyclophanes (Ed.: J. F. Stoddart), Royal Society of Chemistry, Cambridge, 1991;
46. f) for a first example of large C-bridgehead macrobicyclic compounds with homeomorphic isomers, see: A. Wallon, J. Peter-Katalinic, U. Werner, W. M. Müller, F. Vögtle, Chem. Ber. 1990, 123, 375-379; C. Seel, F. Vögtle, Angew. Chem. 1992, 104, 542-563; Angew. Chem. Int. Ed. Engl. 1992, 31, 528-549.
47. f) for a first example of large C-bridgehead macrobicyclic compounds with homeomorphic isomers, see: A. Wallon, J. Peter-Katalinic, U. Werner, W. M. Müller, F. Vögtle, Chem. Ber. 1990, 123, 375-379; C. Seel, F. Vögtle, Angew. Chem. 1992, 104, 542-563; Angew. Chem. Int. Ed. Engl. 1992, 31, 528-549.
48. f) for a first example of large C-bridgehead macrobicyclic compounds with homeomorphic isomers, see: A. Wallon, J. Peter-Katalinic, U. Werner, W. M. Müller, F. Vögtle, Chem. Ber. 1990, 123, 375-379; C. Seel, F. Vögtle, Angew. Chem. 1992, 104, 542-563; Angew. Chem. Int. Ed. Engl. 1992, 31, 528-549.
49. a) F. Vögtle, G. Hohner, E. Weber, J. Chem. Soc. Chem. Commun. 1973, 366-367;
50. b) G. R. Newkome, V. K. Majestic, F. R. Fronczek, Tetrahedron Lett. 1981, 22, 3035-3038;
51. c) G. R. Newkome, V. K. Majestic, F. R. Fronczek, J. L. Atwood, J. Am. Chem. Soc. 1979, 101, 1047-1048;
52. d) J. Jazwinski, J. M. Lehn, D. Lilienbaum, R. Ziessel, J. Guilhem, C. Pascard, J. Chem. Soc. Chem. Commun. 1987, 1691-1694;
53. e) M. G. B. Drew, D. Marrs, J. Hunter, J. Nelson, J. Chem. Soc. Dalton Trans. 1992, 11-18.
54. S. Berger, S. Braun, H.-O. Kalinowski, NMR-Spektroskopie von Nichtmetallen, Vol. 3, Thieme, Stuttgart, New York, 1993.
55. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
56. a) R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37;
57. b) R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426.
58. G. M. Sheldrick, Acta Crystallogr Sect. A 1990, 46, 467-473.
59. G. M. Sheldrick, SHELXL-97, Universität Göttingen, Göttingen (Germany) 1997.
60. L. J. Farugia, University of Glasgow, Glasgow (UK), 1999.