The conformational analysis of phosphine ligands in organometallic complexes. Part 2. Triphenylphosphine coordinated to achiral and prochiral octahedral metal centres

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 1999, Pages 465-473

  Costello, James F ^a   Davies, Stephen G ^b   McNally, David ^a  

^a UNIVERSITY OF THE WEST OF ENGLAND   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001128701     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808794f     Document Type: Article

References (41)

1. Part 1. J. F. Costello and S. G. Davies, J. Chem. Soc., Perkin Trans. 2, 1998, 1683.
2. For example, see E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, Wiley Interscience, 1994, ch. 10-11.
3. Comprehensive Organometallic Chemistry II, Ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, New York, 1995.
4. Part 3. Triphenylphosphine coordinated to stereogenic octahedral metal centres, J. F. Costello and S. G. Davies, in preparation.
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11. 3 coordinated to octahedral metal centres, see J. A. S. Howell, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni-Langerman, Inorg. Chem., 1991, 30, 4685; 1993, 32, 3493: Organometallics, 1993, 12, 1694; J. A. S. Howell, P. C. Yates, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni-Langerman, J. Chem. Soc., Dalton Trans., 1993, 2775.
12. 3 coordinated to octahedral metal centres, see J. A. S. Howell, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni- Langerman, Inorg. Chem., 1991, 30, 4685; 1993, 32, 3493: Organometallics, 1993, 12, 1694; J. A. S. Howell, P. C. Yates, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni-Langerman, J. Chem. Soc., Dalton Trans., 1993, 2775.
13. 3 coordinated to octahedral metal centres, see J. A. S. Howell, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni- Langerman, Inorg. Chem., 1991, 30, 4685; 1993, 32, 3493: Organometallics, 1993, 12, 1694; J. A. S. Howell, P. C. Yates, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni-Langerman, J. Chem. Soc., Dalton Trans., 1993, 2775.
14. 3 coordinated to octahedral metal centres, see J. A. S. Howell, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni- Langerman, Inorg. Chem., 1991, 30, 4685; 1993, 32, 3493: Organometallics, 1993, 12, 1694; J. A. S. Howell, P. C. Yates, M. G. Palin, P. McArdle, D. Cunningham, Z. Goldschmidt, H. E. Gottlieb and D. Hezroni-Langerman, J. Chem. Soc., Dalton Trans., 1993, 2775.
15. For an interesting example, see F. P. Fanizzi, M. Lanfranchi, G. Natile and A. Tiripicchio, Inorg. Chem., 1994, 33, 3331.
16. Equivalent to the transition state for the (a) zero-, (b) one- and (c) three-ring flip stereoisomerisation process. See, R. J. Kurland, I. I. Schuster and A. K. Colter, J. Am. Chem. Soc., 1965, 87, 2279; K. Mislow, Acc. Chem. Res., 1976, 9, 26; D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 7157; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 1535; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 8172; M. R. Kates, J. D. Andose, P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1975, 97, 1772.
17. Equivalent to the transition state for the (a) zero-, (b) one- and (c) three-ring flip stereoisomerisation process. See, R. J. Kurland, I. I. Schuster and A. K. Colter, J. Am. Chem. Soc., 1965, 87, 2279; K. Mislow, Acc. Chem. Res., 1976, 9, 26; D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 7157; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 1535; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 8172; M. R. Kates, J. D. Andose, P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1975, 97, 1772.
18. Equivalent to the transition state for the (a) zero-, (b) one- and (c) three-ring flip stereoisomerisation process. See, R. J. Kurland, I. I. Schuster and A. K. Colter, J. Am. Chem. Soc., 1965, 87, 2279; K. Mislow, Acc. Chem. Res., 1976, 9, 26; D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 7157; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 1535; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 8172; M. R. Kates, J. D. Andose, P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1975, 97, 1772.
19. Equivalent to the transition state for the (a) zero-, (b) one- and (c) three-ring flip stereoisomerisation process. See, R. J. Kurland, I. I. Schuster and A. K. Colter, J. Am. Chem. Soc., 1965, 87, 2279; K. Mislow, Acc. Chem. Res., 1976, 9, 26; D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 7157; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 1535; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 8172; M. R. Kates, J. D. Andose, P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1975, 97, 1772.
20. Equivalent to the transition state for the (a) zero-, (b) one- and (c) three-ring flip stereoisomerisation process. See, R. J. Kurland, I. I. Schuster and A. K. Colter, J. Am. Chem. Soc., 1965, 87, 2279; K. Mislow, Acc. Chem. Res., 1976, 9, 26; D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 7157; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 1535; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 8172; M. R. Kates, J. D. Andose, P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1975, 97, 1772.
21. Equivalent to the transition state for the (a) zero-, (b) one- and (c) three-ring flip stereoisomerisation process. See, R. J. Kurland, I. I. Schuster and A. K. Colter, J. Am. Chem. Soc., 1965, 87, 2279; K. Mislow, Acc. Chem. Res., 1976, 9, 26; D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 7157; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 1535; P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1973, 95, 8172; M. R. Kates, J. D. Andose, P. Finocchiaro, D. Gust and K. Mislow, J. Am. Chem. Soc., 1975, 97, 1772.
22. R. S. Cahn, C. Ingold and V. Prelog, Angew. Chem., Int. Ed. Engl., 1966, 5, 385.
23. S. G. Davies, A. E. Derome and J. P. McNally, J. Am. Chem. Soc., 1991, 113, 2854; S. C. Case-Green, J. F. Costello, S. G. Davies, N. Heaton, C. J. R. Hedgecock, V. M. Humphreys, M. R. Metzler and J. C. Prime, J. Chem. Soc., Perkin Trans, 1, 1994, 933; S. J. Cook, J. F. Costello, S. G. Davies and H. T. Kruk, J. Chem. Soc., Perkin Trans. 1, 1994, 2369; J. F. Costello, S. G. Davies, R. M. Highcock, M. E. C. Polywka, M. W. Poulter, T. Richardson and G. G. Roberts, J. Chem. Soc., Dalton Trans., 1997, 105.
24. S. G. Davies, A. E. Derome and J. P. McNally, J. Am. Chem. Soc., 1991, 113, 2854; S. C. Case-Green, J. F. Costello, S. G. Davies, N. Heaton, C. J. R. Hedgecock, V. M. Humphreys, M. R. Metzler and J. C. Prime, J. Chem. Soc., Perkin Trans, 1, 1994, 933; S. J. Cook, J. F. Costello, S. G. Davies and H. T. Kruk, J. Chem. Soc., Perkin Trans. 1, 1994, 2369; J. F. Costello, S. G. Davies, R. M. Highcock, M. E. C. Polywka, M. W. Poulter, T. Richardson and G. G. Roberts, J. Chem. Soc., Dalton Trans., 1997, 105.
25. S. G. Davies, A. E. Derome and J. P. McNally, J. Am. Chem. Soc., 1991, 113, 2854; S. C. Case-Green, J. F. Costello, S. G. Davies, N. Heaton, C. J. R. Hedgecock, V. M. Humphreys, M. R. Metzler and J. C. Prime, J. Chem. Soc., Perkin Trans, 1, 1994, 933; S. J. Cook, J. F. Costello, S. G. Davies and H. T. Kruk, J. Chem. Soc., Perkin Trans. 1, 1994, 2369; J. F. Costello, S. G. Davies, R. M. Highcock, M. E. C. Polywka, M. W. Poulter, T. Richardson and G. G. Roberts, J. Chem. Soc., Dalton Trans., 1997, 105.
26. S. G. Davies, A. E. Derome and J. P. McNally, J. Am. Chem. Soc., 1991, 113, 2854; S. C. Case-Green, J. F. Costello, S. G. Davies, N. Heaton, C. J. R. Hedgecock, V. M. Humphreys, M. R. Metzler and J. C. Prime, J. Chem. Soc., Perkin Trans, 1, 1994, 933; S. J. Cook, J. F. Costello, S. G. Davies and H. T. Kruk, J. Chem. Soc., Perkin Trans. 1, 1994, 2369; J. F. Costello, S. G. Davies, R. M. Highcock, M. E. C. Polywka, M. W. Poulter, T. Richardson and G. G. Roberts, J. Chem. Soc., Dalton Trans., 1997, 105.
27. Molecular modelling calculations were carried out using the Chem-X package, distributed by Chemical Design Ltd., Oxford Molecular Group, The Medawar Centre, Oxford Science Park, Oxford, UK OX4 4GA.
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31. F. A. Cotton, D. J. Darensbourg and W. H. Ilsley, Inorg. Chem., 1981, 20, 578; F. A. Cotton, D. J. Darensbourg and B. W. S. Kolthammer, Inorg. Chem., 1981, 20, 4440; A. Martin and A. G. Orpen, J. Am. Chem. Soc., 1996, 118, 1470.
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34. M. J. Aroney, I. E. Buys, M. S. Davies and T. W. Hambley, J. Chem. Soc., Dalton Trans., 1994, 2827; K. J. Lee and T. L. Brown, Inorg. Chem., 1992, 31, 289; J. Polowin, S. C. Mackie and M. C. Baird, Organometallics, 1992, 11, 3724.
35. Originally, the conformational analysis of such transition metal complexes was based upon a pseudo-tetrahedral geometry. This led to the formulation of erroneous analyses and predictions, which were inconsistent with experimental data. For further detailed discussions, see: J. I. Seeman and S. G. Davies, J. Chem. Soc., Chem. Commun., 1984, 1019; J. Am. Chem. Soc., 1985, 107, 6522. A. D. Cameron, M. C. Baird, J. I. Seeman and S. G. Davies, J. Chem. Soc., Dalton Trans., 1985, 2691; S. G. Davies, I. M. Dordor-Hedgecock, K. H. Sutton and M. Whittaker, J. Am. Chem. Soc., 1987, 109, 5711.
36. Originally, the conformational analysis of such transition metal complexes was based upon a pseudo-tetrahedral geometry. This led to the formulation of erroneous analyses and predictions, which were inconsistent with experimental data. For further detailed discussions, see: J. I. Seeman and S. G. Davies, J. Chem. Soc., Chem. Commun., 1984, 1019; J. Am. Chem. Soc., 1985, 107, 6522. A. D. Cameron, M. C. Baird, J. I. Seeman and S. G. Davies, J. Chem. Soc., Dalton Trans., 1985, 2691; S. G. Davies, I. M. Dordor-Hedgecock, K. H. Sutton and M. Whittaker, J. Am. Chem. Soc., 1987, 109, 5711.
37. Originally, the conformational analysis of such transition metal complexes was based upon a pseudo-tetrahedral geometry. This led to the formulation of erroneous analyses and predictions, which were inconsistent with experimental data. For further detailed discussions, see: J. I. Seeman and S. G. Davies, J. Chem. Soc., Chem. Commun., 1984, 1019; J. Am. Chem. Soc., 1985, 107, 6522. A. D. Cameron, M. C. Baird, J. I. Seeman and S. G. Davies, J. Chem. Soc., Dalton Trans., 1985, 2691; S. G. Davies, I. M. Dordor-Hedgecock, K. H. Sutton and M. Whittaker, J. Am. Chem. Soc., 1987, 109, 5711.
38. Originally, the conformational analysis of such transition metal complexes was based upon a pseudo-tetrahedral geometry. This led to the formulation of erroneous analyses and predictions, which were inconsistent with experimental data. For further detailed discussions, see: J. I. Seeman and S. G. Davies, J. Chem. Soc., Chem. Commun., 1984, 1019; J. Am. Chem. Soc., 1985, 107, 6522. A. D. Cameron, M. C. Baird, J. I. Seeman and S. G. Davies, J. Chem. Soc., Dalton Trans., 1985, 2691; S. G. Davies, I. M. Dordor-Hedgecock, K. H. Sutton and M. Whittaker, J. Am. Chem. Soc., 1987, 109, 5711.
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