Platinum(0) complexes of chiral diphosphines: Enantioface-selective binding of trans-stilbene

Organometallics

Volumn 17, Issue 7, 1998, Pages 1412-1419

  Wicht, Denyce K ^a   Zhuravel, Michael A ^a   Gregush, Ronald V ^a   Glueck, David S ^a   Guzei, Ilia A ^b   Liable Sands, Louise M ^b   Rheingold, Arnold L ^b  

^a Dartmouth College   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001452781     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971000j     Document Type: Article

References (42)

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5. For related studies, see: (a) Brown, J. M.; Perez-Torrente, J. J.; Alcock, N. W. Organometallics 1995, 14, 1195-1203. (b) Paganelli, S.; Matteoli, U.; Scrivanti, A. J. Organomet. Chem. 1990, 397, 119-125.
6. For related studies, see: (a) Brown, J. M.; Perez-Torrente, J. J.; Alcock, N. W. Organometallics 1995, 14, 1195-1203. (b) Paganelli, S.; Matteoli, U.; Scrivanti, A. J. Organomet. Chem. 1990, 397, 119-125.
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16. 2), but these were not obtained pure (see p 5139).
17. 2.
18. 2 under ethylene.
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20. See Scheme 1 for the structure of Diop. (a) Reference 7c
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24. See refs 8 and 9 and for a recent example: Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156-8157.
25. See Scheme 1 for ligand structures. Most of these dichlorides have been reported previously, dppe: Hudson, M. J.; Nyholm, R. S.; Stiddard, M. H. B. J. Chem. Soc. A 1968, 40-43. dppf: Bandini, A. L.; Bandftelli, G.; Cinellu, M. A.; Sanna, G.; Minghetti, G.; Demartin, F.; Manassero, M. Inorg. Chem. 1989, 28, 404-410 and ref 1 therein. Chiraphos: Morandini, F.; Consiglio, G.; Piccolo, O. Inorg. Chim. Acta 1982, 57, 15-19. Diop: Gramlich, V.; Consiglio, G. Helv. Chim. Acta 1979, 62, 1016-1024.
26. See Scheme 1 for ligand structures. Most of these dichlorides have been reported previously, dppe: Hudson, M. J.; Nyholm, R. S.; Stiddard, M. H. B. J. Chem. Soc. A 1968, 40-43. dppf: Bandini, A. L.; Bandftelli, G.; Cinellu, M. A.; Sanna, G.; Minghetti, G.; Demartin, F.; Manassero, M. Inorg. Chem. 1989, 28, 404-410 and ref 1 therein. Chiraphos: Morandini, F.; Consiglio, G.; Piccolo, O. Inorg. Chim. Acta 1982, 57, 15-19. Diop: Gramlich, V.; Consiglio, G. Helv. Chim. Acta 1979, 62, 1016-1024.
27. See Scheme 1 for ligand structures. Most of these dichlorides have been reported previously, dppe: Hudson, M. J.; Nyholm, R. S.; Stiddard, M. H. B. J. Chem. Soc. A 1968, 40-43. dppf: Bandini, A. L.; Bandftelli, G.; Cinellu, M. A.; Sanna, G.; Minghetti, G.; Demartin, F.; Manassero, M. Inorg. Chem. 1989, 28, 404-410 and ref 1 therein. Chiraphos: Morandini, F.; Consiglio, G.; Piccolo, O. Inorg. Chim. Acta 1982, 57, 15-19. Diop: Gramlich, V.; Consiglio, G. Helv. Chim. Acta 1979, 62, 1016-1024.
28. See Scheme 1 for ligand structures. Most of these dichlorides have been reported previously, dppe: Hudson, M. J.; Nyholm, R. S.; Stiddard, M. H. B. J. Chem. Soc. A 1968, 40-43. dppf: Bandini, A. L.; Bandftelli, G.; Cinellu, M. A.; Sanna, G.; Minghetti, G.; Demartin, F.; Manassero, M. Inorg. Chem. 1989, 28, 404-410 and ref 1 therein. Chiraphos: Morandini, F.; Consiglio, G.; Piccolo, O. Inorg. Chim. Acta 1982, 57, 15-19. Diop: Gramlich, V.; Consiglio, G. Helv. Chim. Acta 1979, 62, 1016-1024.
29. Pt-P = 3667 H2.
30. Messmer, G. G.; Amma, E. L.; Ibers, J. A. Inorg. Chem. 1967, 6, 725-730.
31. For examples of photochemical isomerization, see: (a) Wrighton, M.; Hammond, G. S.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3285-3287. (b) Sakaki, S.; Okitaka, I.; Ohkubo, K. Inorg. Chem. 1984, 23, 198-203. For thermal processes, see, for example: (c) Manuel, T. A. J. Org. Chem. 1962, 27, 3941-3945. (d) Castiglione, M.; Giordano, R.; Sappa, E. J. Organomet. Chem. 1991, 407, 377-389. (e) Todres, Z. V.; Ionina, E. A.; Pombeiro, A. J. L. J. Organomet. Chem. 1992, 438, C23-C25. Here, a referee suggested another plausible mechanism for isomerization, reversible protonation of the Pt complex by catalytic adventitious acid.
32. For examples of photochemical isomerization, see: (a) Wrighton, M.; Hammond, G. S.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3285-3287. (b) Sakaki, S.; Okitaka, I.; Ohkubo, K. Inorg. Chem. 1984, 23, 198-203. For thermal processes, see, for example: (c) Manuel, T. A. J. Org. Chem. 1962, 27, 3941-3945. (d) Castiglione, M.; Giordano, R.; Sappa, E. J. Organomet. Chem. 1991, 407, 377-389. (e) Todres, Z. V.; Ionina, E. A.; Pombeiro, A. J. L. J. Organomet. Chem. 1992, 438, C23-C25. Here, a referee suggested another plausible mechanism for isomerization, reversible protonation of the Pt complex by catalytic adventitious acid.
33. For examples of photochemical isomerization, see: (a) Wrighton, M.; Hammond, G. S.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3285-3287. (b) Sakaki, S.; Okitaka, I.; Ohkubo, K. Inorg. Chem. 1984, 23, 198-203. For thermal processes, see, for example: (c) Manuel, T. A. J. Org. Chem. 1962, 27, 3941-3945. (d) Castiglione, M.; Giordano, R.; Sappa, E. J. Organomet. Chem. 1991, 407, 377-389. (e) Todres, Z. V.; Ionina, E. A.; Pombeiro, A. J. L. J. Organomet. Chem. 1992, 438, C23-C25. Here, a referee suggested another plausible mechanism for isomerization, reversible protonation of the Pt complex by catalytic adventitious acid.
34. For examples of photochemical isomerization, see: (a) Wrighton, M.; Hammond, G. S.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3285-3287. (b) Sakaki, S.; Okitaka, I.; Ohkubo, K. Inorg. Chem. 1984, 23, 198-203. For thermal processes, see, for example: (c) Manuel, T. A. J. Org. Chem. 1962, 27, 3941-3945. (d) Castiglione, M.; Giordano, R.; Sappa, E. J. Organomet. Chem. 1991, 407, 377-389. (e) Todres, Z. V.; Ionina, E. A.; Pombeiro, A. J. L. J. Organomet. Chem. 1992, 438, C23-C25. Here, a referee suggested another plausible mechanism for isomerization, reversible protonation of the Pt complex by catalytic adventitious acid.
35. For examples of photochemical isomerization, see: (a) Wrighton, M.; Hammond, G. S.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3285-3287. (b) Sakaki, S.; Okitaka, I.; Ohkubo, K. Inorg. Chem. 1984, 23, 198-203. For thermal processes, see, for example: (c) Manuel, T. A. J. Org. Chem. 1962, 27, 3941-3945. (d) Castiglione, M.; Giordano, R.; Sappa, E. J. Organomet. Chem. 1991, 407, 377-389. (e) Todres, Z. V.; Ionina, E. A.; Pombeiro, A. J. L. J. Organomet. Chem. 1992, 438, C23-C25. Here, a referee suggested another plausible mechanism for isomerization, reversible protonation of the Pt complex by catalytic adventitious acid.
36. For related observations in Ni(0) complexes of chiral diphosphinites, see: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869-9882.
37. 3, 1/2dppe, and 1/2dppb are 3721, 3303, and 3524 Hz, respectively. See ref 7.
38. Schwartz, D. J.; Andersen, R. A. J. Am. Chem. Soc. 1995, 117, 4014-4025.
39. Knobler, C. B.; Kaesz, H. D.; Minghetti, G.; Bandini, A. L.; Banditelli, G.; Bonati, F. Inorg. Chem. 1983, 22, 2324-2331.
40. Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174-4181.
41. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521-6528.
42. Walker, N.; Stuart, D. Acta Crystallogr. 1983, A39, 158.