PH-Functional Phosphines with 1,1′-Biphenyl-2,2′-bis(methylene) and 1,1′-Binaphthyl-2,2′-bis(methylene) Backbones

Inorganic Chemistry

Volumn 37, Issue 25, 1998, Pages 6408-6417

  Bitterer, Frank ^a   Herd, Oliver ^a   Kühnel, Michael ^a   Stelzer, Othmar ^a   Weferling, Norbert ^b   Sheldrick, William S ^c   Hahn, Jutta ^d   Nagel, Sabine ^d   Rösch, Notker ^d  

^a UNIVERSITY OF WUPPERTAL   (Germany)

^b CLARIANT PRODUKTE DEUTSCHLAND GMBH   (Germany)

^c RUHR UNIVERSITY BOCHUM   (Germany)

^d TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000255703     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic980346z     Document Type: Article

References (74)

1. Casey, C. P.; Whiteker, G. T.; Campana, C. F.; Powell, D. R. Inorg. Chem. 1990, 29, 3376. Herrmann, W. A.; Kohlpaintner, C. W.; Herdtweck, E.; Kiprof, P. Inorg. Chem. 1991, 30, 4271. Devon, T. J.; Phillips, G. W.; Puckette, T. A.; Stavinoha, J. L.; Vanderbilt, J. J. U.S. Patent 4,694,109, Sept 15, 1987, Eastman Kodak Co. Puckette, T. A.; Devon, T. J.; Phillips, G. W.; Stavinoha, J. L. U.S. Patent 4,879,416, July 11, 1989, Eastman Kodak Co.
2. Casey, C. P.; Whiteker, G. T.; Campana, C. F.; Powell, D. R. Inorg. Chem. 1990, 29, 3376. Herrmann, W. A.; Kohlpaintner, C. W.; Herdtweck, E.; Kiprof, P. Inorg. Chem. 1991, 30, 4271. Devon, T. J.; Phillips, G. W.; Puckette, T. A.; Stavinoha, J. L.; Vanderbilt, J. J. U.S. Patent 4,694,109, Sept 15, 1987, Eastman Kodak Co. Puckette, T. A.; Devon, T. J.; Phillips, G. W.; Stavinoha, J. L. U.S. Patent 4,879,416, July 11, 1989, Eastman Kodak Co.
3. Casey, C. P.; Whiteker, G. T.; Campana, C. F.; Powell, D. R. Inorg. Chem. 1990, 29, 3376. Herrmann, W. A.; Kohlpaintner, C. W.; Herdtweck, E.; Kiprof, P. Inorg. Chem. 1991, 30, 4271. Devon, T. J.; Phillips, G. W.; Puckette, T. A.; Stavinoha, J. L.; Vanderbilt, J. J. U.S. Patent 4,694,109, Sept 15, 1987, Eastman Kodak Co. Puckette, T. A.; Devon, T. J.; Phillips, G. W.; Stavinoha, J. L. U.S. Patent 4,879,416, July 11, 1989, Eastman Kodak Co.
4. Casey, C. P.; Whiteker, G. T.; Campana, C. F.; Powell, D. R. Inorg. Chem. 1990, 29, 3376. Herrmann, W. A.; Kohlpaintner, C. W.; Herdtweck, E.; Kiprof, P. Inorg. Chem. 1991, 30, 4271. Devon, T. J.; Phillips, G. W.; Puckette, T. A.; Stavinoha, J. L.; Vanderbilt, J. J. U.S. Patent 4,694,109, Sept 15, 1987, Eastman Kodak Co. Puckette, T. A.; Devon, T. J.; Phillips, G. W.; Stavinoha, J. L. U.S. Patent 4,879,416, July 11, 1989, Eastman Kodak Co.
5. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131.
6. (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
7. (b) Tamao, K.; Yamamoto, H.; Matsumoto, H.; Miyake, N.; Hayashi, T.; Kumada, M. Tetrahedron Lett. 1977, 1389. Puckette, T. A. Eur. Pat. 386,105, Oct 31, 1988, Eastman Kodak Co.
8. (b) Tamao, K.; Yamamoto, H.; Matsumoto, H.; Miyake, N.; Hayashi, T.; Kumada, M. Tetrahedron Lett. 1977, 1389. Puckette, T. A. Eur. Pat. 386,105, Oct 31, 1988, Eastman Kodak Co.
9. Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Manassero, M. Tetrahedron: Asymmetry 1994, 5, 511.
10. (a) Gladiali, S.; Fabbri, D. Chem. Ber./Recueil 1997, 130, 543. Watson, A. A.; Willis, A. C.; Wild, S. B. J. Organomet. Chem. 1993, 445, 71. Tani, K.; Tashiro, H.; Yoshida, M.; Yamagata, T. J. Organomet. Chem. 1994, 469, 229.
11. (a) Gladiali, S.; Fabbri, D. Chem. Ber./Recueil 1997, 130, 543. Watson, A. A.; Willis, A. C.; Wild, S. B. J. Organomet. Chem. 1993, 445, 71. Tani, K.; Tashiro, H.; Yoshida, M.; Yamagata, T. J. Organomet. Chem. 1994, 469, 229.
12. (a) Gladiali, S.; Fabbri, D. Chem. Ber./Recueil 1997, 130, 543. Watson, A. A.; Willis, A. C.; Wild, S. B. J. Organomet. Chem. 1993, 445, 71. Tani, K.; Tashiro, H.; Yoshida, M.; Yamagata, T. J. Organomet. Chem. 1994, 469, 229.
13. (b) Dore, A.; Fabbri, D.; Gladiali, S.; De Lucchi, O. J. Chem. Soc., Chem. Commun. 1993, 1124. Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Valle, G. J. Org. Chem. 1994, 59, 6363.
14. (b) Dore, A.; Fabbri, D.; Gladiali, S.; De Lucchi, O. J. Chem. Soc., Chem. Commun. 1993, 1124. Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Valle, G. J. Org. Chem. 1994, 59, 6363.
15. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Rosini, C.; Franzini, L.; Raffaeli, A.; Salvadori, P. Synthesis 1992, 503.
16. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Rosini, C.; Franzini, L.; Raffaeli, A.; Salvadori, P. Synthesis 1992, 503.
17. Noyori, R. Chem. Soc. Rev. 1989, 18, 187. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3176. Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461.
18. Noyori, R. Chem. Soc. Rev. 1989, 18, 187. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3176. Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461.
19. Noyori, R. Chem. Soc. Rev. 1989, 18, 187. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3176. Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461.
20. Frohning, C. D.; Kohlpaintner, C. W. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornus, B., Herrmann, W. A., Eds.; VCH Verlagsgesellschaft mbH: Weinheim, 1996; Vol. 1, p 29. Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183.
21. Frohning, C. D.; Kohlpaintner, C. W. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornus, B., Herrmann, W. A., Eds.; VCH Verlagsgesellschaft mbH: Weinheim, 1996; Vol. 1, p 29. Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183.
22. Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Catal. Today 1998, 42, 413.
23. Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69. Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Catal. Today 1998, 42, 413.
24. Bitterer, F.; Herd, O.; Hessler, A.; Kühnel, M.; Rettig, K.; Stelzer, O.; Sheldrick, W. S.; Nagel, S.; Rösch, N. Inorg. Chem. 1996, 35, 4103. Herd, O.; Langhans, K. P.; Stelzer, O.; Weferling, N.; Sheldrick, W. S. Angew. Chem., Int. Ed. 1993, 32, 1058. Herd, O.; Hessler, A.; Langhans, K. P.; Stelzer, O.; Sheldrick, W. S.; Weferling, N. J. Organomet. Chem. 1994, 475, 99.
25. Bitterer, F.; Herd, O.; Hessler, A.; Kühnel, M.; Rettig, K.; Stelzer, O.; Sheldrick, W. S.; Nagel, S.; Rösch, N. Inorg. Chem. 1996, 35, 4103. Herd, O.; Langhans, K. P.; Stelzer, O.; Weferling, N.; Sheldrick, W. S. Angew. Chem., Int. Ed. 1993, 32, 1058. Herd, O.; Hessler, A.; Langhans, K. P.; Stelzer, O.; Sheldrick, W. S.; Weferling, N. J. Organomet. Chem. 1994, 475, 99.
26. Bitterer, F.; Herd, O.; Hessler, A.; Kühnel, M.; Rettig, K.; Stelzer, O.; Sheldrick, W. S.; Nagel, S.; Rösch, N. Inorg. Chem. 1996, 35, 4103. Herd, O.; Langhans, K. P.; Stelzer, O.; Weferling, N.; Sheldrick, W. S. Angew. Chem., Int. Ed. 1993, 32, 1058. Herd, O.; Hessler, A.; Langhans, K. P.; Stelzer, O.; Sheldrick, W. S.; Weferling, N. J. Organomet. Chem. 1994, 475, 99.
27. Langhans, K. P.; Stelzer, O.; Weferling, N. Chem. Ber. 1990, 123, 995. Stelzer, O.; Langhans, K. P.; Svara, J.; Weferling, N. Eur. Pat. 307,702, Mar 22, 1989; Eur. Pat. 307,717, Mar 22, 1989; U.S. Patent 5,003,108, Mar 26, 1991, Hoechst AG.
28. Langhans, K. P.; Stelzer, O.; Weferling, N. Chem. Ber. 1990, 123, 995. Stelzer, O.; Langhans, K. P.; Svara, J.; Weferling, N. Eur. Pat. 307,702, Mar 22, 1989; Eur. Pat. 307,717, Mar 22, 1989; U.S. Patent 5,003,108, Mar 26, 1991, Hoechst AG.
29. Langhans, K. P.; Stelzer, O.; Weferling, N. Chem. Ber. 1990, 123, 995. Stelzer, O.; Langhans, K. P.; Svara, J.; Weferling, N. Eur. Pat. 307,702, Mar 22, 1989; Eur. Pat. 307,717, Mar 22, 1989; U.S. Patent 5,003,108, Mar 26, 1991, Hoechst AG.
30. Langhans, K. P.; Stelzer, O.; Weferling, N. Chem. Ber. 1990, 123, 995. Stelzer, O.; Langhans, K. P.; Svara, J.; Weferling, N. Eur. Pat. 307,702, Mar 22, 1989; Eur. Pat. 307,717, Mar 22, 1989; U.S. Patent 5,003,108, Mar 26, 1991, Hoechst AG.
31. Chong, J. M.; MacDonald, G. K.; Park, S. B.; Wilkinson, S. H. J. Org. Chem. 1993, 55, 1266.
32. Maigrot, N.; Mazaleyrat, J. P. Synthesis 1985, 317. Bestmann, H. J.; Both, W. Chem. Ber. 1974, 107, 2923, 2926.
33. Maigrot, N.; Mazaleyrat, J. P. Synthesis 1985, 317. Bestmann, H. J.; Both, W. Chem. Ber. 1974, 107, 2923, 2926.
34. Mathey, F. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Georg Thieme Verlag: Stuttgart, 1990; p 33.
35. (a) Becker, G.; Hölderich, W. Chem. Ber. 1975, 108, 2484.
36. (b) Fritz, G.; Hölderich, W. Z. Anorg. Allg. Chem. 1976, 422, 104. Schumann, H.; Rösch, L.; Schmidt-Fritsche, W. Chem. Ztg. 1977, 101, 156.
37. (b) Fritz, G.; Hölderich, W. Z. Anorg. Allg. Chem. 1976, 422, 104. Schumann, H.; Rösch, L.; Schmidt-Fritsche, W. Chem. Ztg. 1977, 101, 156.
38. (c) Maier, L. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972; Vol. 1, p 1.
39. Fuji, K.; Yamada, T.; Fujita, E. Org. Magn. Reson. 1981, 4, 250.
40. (a) Berger, S.; Braun, S.; Kalinowski, H. O. NMR-Spektroskopie von Nichtmetallen; Georg Thieme Verlag: Stuttgart, 1993; Vol 3.
41. 13C NMR-Spektroskopie; Georg Thieme Verlag: Stuttgart, 1984.
42. Kessler, H.; Gehrke, M.; Griesinger, C. Angew. Chem., Int. Ed. 1988, 27, 490. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy; Oxford University Press: Oxford, New York, Toronto, 1987.
43. Kessler, H.; Gehrke, M.; Griesinger, C. Angew. Chem., Int. Ed. 1988, 27, 490. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy; Oxford University Press: Oxford, New York, Toronto, 1987.
44. (a) Hawkins, J. M.; Fu, G. C. J. Org. Chem. 1986, 51, 2820.
45. (b) Stara, I. G.; Stary, I.; Tichy, M.; Zavada, J.; Fiedler, P. J. Org. Chem. 1994, 59, 1326,
46. (c) Noyori, R.; Sano, N.; Murata, S.; Okamoto, Y.; Yuki, H.; Ito, T. Tetrahedron Lett. 1982, 23, 2969. Engelhardt, L. M.; Leung, W. P.; Raston, C. L.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1984, 331.
47. (c) Noyori, R.; Sano, N.; Murata, S.; Okamoto, Y.; Yuki, H.; Ito, T. Tetrahedron Lett. 1982, 23, 2969. Engelhardt, L. M.; Leung, W. P.; Raston, C. L.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1984, 331.
48. Issleib, K.; Kühne, U.; Thorausch, P. Synth. React. Inorg. Met.-Org. Chem. 1987, 17, 275. Issleib, K.; Thorausch, P. Phosphorus Sulfur Relat. Elem. 1977, 3, 203; 1978, 4, 137.
49. Issleib, K.; Kühne, U.; Thorausch, P. Synth. React. Inorg. Met.-Org. Chem. 1987, 17, 275. Issleib, K.; Thorausch, P. Phosphorus Sulfur Relat. Elem. 1977, 3, 203; 1978, 4, 137.
50. Issleib, K.; Kühne, U.; Thorausch, P. Synth. React. Inorg. Met.-Org. Chem. 1987, 17, 275. Issleib, K.; Thorausch, P. Phosphorus Sulfur Relat. Elem. 1977, 3, 203; 1978, 4, 137.
51. Cotton, F. A.; Kraihanzel, C. S. J. Am. Chem. Soc. 1962, 84, 4432. Darensbourg, D. J.; Nelson, H. H.; Hyde, C. L. Inorg. Chem. 1974, 13, 2135.
52. Cotton, F. A.; Kraihanzel, C. S. J. Am. Chem. Soc. 1962, 84, 4432. Darensbourg, D. J.; Nelson, H. H.; Hyde, C. L. Inorg. Chem. 1974, 13, 2135.
53. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244. Imamoto, T. Pure Appl. Chem. 1993, 65, 655. Juge, S.; Stephan, M.; Merdes, R.; Genet, J. P.; HalutDesportes, S. J. Chem. Soc., Chem. Commun. 1993, 531.
54. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244. Imamoto, T. Pure Appl. Chem. 1993, 65, 655. Juge, S.; Stephan, M.; Merdes, R.; Genet, J. P.; HalutDesportes, S. J. Chem. Soc., Chem. Commun. 1993, 531.
55. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244. Imamoto, T. Pure Appl. Chem. 1993, 65, 655. Juge, S.; Stephan, M.; Merdes, R.; Genet, J. P.; HalutDesportes, S. J. Chem. Soc., Chem. Commun. 1993, 531.
56. Berlin, K. D.; Butler, G. B. J. Org. Chem. 1961, 26, 2537. Rabinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623.
57. Berlin, K. D.; Butler, G. B. J. Org. Chem. 1961, 26, 2537. Rabinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623.
58. (a) Hietkamp, S.; Lebbe, T.; Spiegel, G. U.; Stelzer, O. Z. Naturforsch. 1987, 42b, 177.
59. (b) Hessler, A.; Fischer, J.; Kucken, S.; Stelzer, O. Chem. Ber. 1994, 127, 481.
60. Scherer, J.; Huttner, G.; Büchner, M.; Bakos, J. J. Organomet. Chem. 1996, 520, 45.
61. Regnat, D. D.E. 4,433,952, 1996, Hoechst AG.
62. Desper, J. M.; Gellmann, S. H.; Wolf, R. E.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Desper, J. M.; Vyvyan, J. R.; Mayer, M. J.; Ochrymovycz, L. A.; Gellman, S. H. Inorg. Chem. 1993, 32, 381.
63. Desper, J. M.; Gellmann, S. H.; Wolf, R. E.; Cooper, S. R. J. Am. Chem. Soc. 1991, 113, 8663. Desper, J. M.; Vyvyan, J. R.; Mayer, M. J.; Ochrymovycz, L. A.; Gellman, S. H. Inorg. Chem. 1993, 32, 381.
64. (a) Bandarage, U. K.; Hanton, L. R.; Smith, R. A. J. Tetrahedron 1995, 51, 787.
65. (b) Gilheany, D. G. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; J. Wiley and Sons: Chichester, 1990; Vol. 1, p 9.
66. Maple, J.; Dinur, U.; Hagler, A. T. Proc. Natl. Acad. Sci. U.S.A. 1988, 55, 5350.
67. Program Discover, Version 2.3.5; Biosym Technologies: San Diego, 1993.
68. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221; 1991, 12, 320.
69. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221; 1991, 12, 320.
70. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221; 1991, 12, 320.
71. Perrin, D. D.; Amarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: Oxford, 1966.
72. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, 1974; Vol. 4.
73. Rauhut, G.; Alex, A.; Chandrasekhar, J.; Steinke, T.; Sauer, W.; Beck, B.; Clark, T. VAMP 5.5 Manual, Centrum für Computer-Chemie der Universität Erlangen-Nürnberg, 1994.
74. Herrmann, W. A.; Schmid, R.; Kohlpaintner, C. W.; Priermeier, T. Organometallics 1995, 14, 1961.