Synthesis and X-ray crystal structures of silacalix[n]phosphinines: The first sp2-based phosphorus macrocycles

Chemistry - A European Journal

Volumn 5, Issue 7, 1999, Pages 2109-2118

  Avarvari, Narcis ^a   Maigrot, Nicole ^a   Ricard, Louis ^a   Mathey, François ^a   Le Floch, Pascal ^a  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

Cycloadditions; Heterocycles; Macrocycles; Phosphinines; Phosphorus; Silicon

Indexed keywords

1,3,2 DIAZAPHOSPHININE; DIMETHYLSILACALIX[3]PHOSPHININE; DIMETHYLSILACALIX[4]PHOSPHININE; MACROCYCLIC COMPOUND; PHOSPHININE; PHOSPHORUS; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; POLYMERIZATION; PROTEIN STABILITY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0033064997     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990702)5:7<2109::AID-CHEM2109>3.0.CO;2-Q     Document Type: Article

References (84)

1. a) Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990;
2. b) K. B. Dillon, F. Mathey, J F. Nixon, Phosphorus: The Carbon Copy, Wiley, Chichester, 1998.
3. a) R. Appel, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, pp. 157-219;
4. b) M. Regitz, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O J. Scherer), Thieme, Stuttgart, 1990, pp. 58-111;
5. c) J. F. Nixon, Coord. Chem. Rev. 1995, 145, 201;
6. d) M. Regitz, Chem. Rev. 1990, 90, 191.
7. a) A. Jouaiti, M. Geoffroy, G. Bernardinelli, Tetrahedron Lett. 1992, 33, 5071;
8. b) A. Jouaiti, M. Geoffroy, G. Terron, G. Bernardinelli, J. Chem. Soc. Chem. Commun. 1992, 155;
9. c) A. Jouaiti, M. Geoffroy, G. Terron, G Bernardinelli, Tetrahedron Lett 1993, 34, 3413;
10. d) A. Jouaiti, M. Geoffroy, G. Bernardinelli, J. Chem. Soc. Dalton Trans. 1994, 1685;
11. e) A. Jouaiti, M. Geoffroy, G. Terron, G. Bernardinelli, J. Am. Chem. Soc. 1995, 117, 2251;
12. f) A. Jouaiti, M. Geoffroy, G. Bernardinelli, Chem. Commun 1996, 437;
13. g) M. van de Sluis, J. B. Vit, F. Bickelhaupt, Organometallics, 1996, 15, 174;
14. h) M. van der Sluis, V. Beverwijk, A. Termaten, E. Gavrilova, F. Bickelhaupt, H. Kooijman, N Veldman, A. Spek, Organometallics, 1997, 16, 1144.
15. See for example: a) K. K. Baldridge, M S. Gordon, J. Am. Chem Soc. 1988, 110, 4204, b) L. Nyulaszi, G. Keglevich, Heteroatom Chem. 1994, 5, 131; c) B. Goldfuss, P. v. R. Schleyer, F. Hampel, Organometallics, 1996, 15, 1755; d) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem 1995, 107, 332; Angew Chem Int. Ed. Engl. 1995, 34, 337
16. See for example: a) K. K. Baldridge, M S. Gordon, J. Am. Chem Soc. 1988, 110, 4204, b) L. Nyulaszi, G. Keglevich, Heteroatom Chem. 1994, 5, 131; c) B. Goldfuss, P. v. R. Schleyer, F. Hampel, Organometallics, 1996, 15, 1755; d) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem 1995, 107, 332; Angew Chem Int. Ed. Engl. 1995, 34, 337
17. See for example: a) K. K. Baldridge, M S. Gordon, J. Am. Chem Soc. 1988, 110, 4204, b) L. Nyulaszi, G. Keglevich, Heteroatom Chem. 1994, 5, 131; c) B. Goldfuss, P. v. R. Schleyer, F. Hampel, Organometallics, 1996, 15, 1755; d) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem 1995, 107, 332; Angew Chem Int. Ed. Engl. 1995, 34, 337
18. See for example: a) K. K. Baldridge, M S. Gordon, J. Am. Chem Soc. 1988, 110, 4204, b) L. Nyulaszi, G. Keglevich, Heteroatom Chem. 1994, 5, 131; c) B. Goldfuss, P. v. R. Schleyer, F. Hampel, Organometallics, 1996, 15, 1755; d) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem 1995, 107, 332; Angew Chem Int. Ed. Engl. 1995, 34, 337
19. See for example: a) K. K. Baldridge, M S. Gordon, J. Am. Chem Soc. 1988, 110, 4204, b) L. Nyulaszi, G. Keglevich, Heteroatom Chem. 1994, 5, 131; c) B. Goldfuss, P. v. R. Schleyer, F. Hampel, Organometallics, 1996, 15, 1755; d) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuss, Angew. Chem 1995, 107, 332; Angew Chem Int. Ed. Engl. 1995, 34, 337
20. For reviews on phosphinine chemistry see: a) G. Märkl, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds., M. Regitz, O. J Scherer), Thieme, Stuttgart, 1990, pp. 220-257; b) G. G. Hewitt, in Comprehensive Heterocyclic Chemistry II, Vol. 5 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven) Pergamon, New York, 1996, p 639; c) K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy. Wiley, Chichester, 1998. pp. 235-256.
21. For reviews on phosphinine chemistry see: a) G. Märkl, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds., M. Regitz, O. J Scherer), Thieme, Stuttgart, 1990, pp. 220-257; b) G. G. Hewitt, in Comprehensive Heterocyclic Chemistry II, Vol. 5 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven) Pergamon, New York, 1996, p 639; c) K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy. Wiley, Chichester, 1998. pp. 235-256.
22. For reviews on phosphinine chemistry see: a) G. Märkl, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds., M. Regitz, O. J Scherer), Thieme, Stuttgart, 1990, pp. 220-257; b) G. G. Hewitt, in Comprehensive Heterocyclic Chemistry II, Vol. 5 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven) Pergamon, New York, 1996, p 639; c) K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy. Wiley, Chichester, 1998. pp. 235-256.
23. F. Mathey, Coord. Chem. Rev. 1994, 137, 1.
24. A. Schmidpeter, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz and O. J. Scherer), Thieme, Stuttgart, 1990, pp. 258-286.
25. J. Waluk, H.-P. Klein, A. J. Ashe III, J. Michl, Organometallics, 1989, 8, 2804.
26. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
27. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
28. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
29. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
30. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
31. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
32. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
33. For references on the use of phosphaferrocenes and phosphinines as ligands in homogeneous catalysis see: for phosphaferrocenes: a) C. E. Garrett, G. C. Fu, J Org. Chem. 1997, 62, 4534, b) S. Qiao, D. A. Hoic, G. C. Fu, Organometallics, 1998, 17, 773; c) S. Qiao, G. C. Fu, J Org. Chem. 1998, 63, 4168; d) C. Ganter, C. Glinsböckel, B. Ganter, Eur. J. Inorg. Chem. 1998, 1, 1163. For phosphinines: a) B. Breit, Chem. Commun. 1996, 2071, b) B. Breit, R. Winde, K. Harms, J Chem. Soc. Perkin Trans. 1, 1997, 2681; c) F. Knoch, F. Kremer, U. Schmidt, U. Zenneck, P. Le Floch, F. Mathey, Organometallics, 1996, 25, 831; d) P. Le Floch, F. Knoch, F. Kremer, F. Mathey, J. Scholz, W. Scholz, K-H. Thiele, U. Zenneck, Eur. J. Inorg. Chem. 1998, 1, 119.
34. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
35. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
36. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
37. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
38. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
39. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
40. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
41. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
42. For references on the use of phosphinines in coordination chemistry: a) C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wočadlo, Angew. Chem. 1992, 104, 1388; Angew. Chem. Int. Ed. Engl. 1992, 31, 1343; b) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, K. Harms, S. Wocadlo, J. Pebler, J. Am. Chem Soc. 1994, 116, 6217; c) C. Elschenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa, S. Wocadlo, J. Organomet. Chem. 1993, 459, 157; d) P. Le Floch, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Inorg. Chem. 1995, 34, 11; e) F. Mathey, P. Le Floch, Chem. Ber. 1996, 129, 263; f) P. Rosa, L. Ricard, P Le Floch, F. Mathey, G. Sini, O. Eisenstein, Inorg. Chem. 1998, 37, 3154, g) P. Le Floch, S. Mansuy, L. Ricard, F. Mathey, A. Jutand, C. Amatore, Organometallics, 1996, 15, 3267; h) F. Mathey, P. Le Floch, Coord. Chem. Rev. 1998, 179-180, 771.
43. See for example: a) P. Le Floch, D. Carmichael, L. Ricard, F. Mathey, J. Am. Chem Soc. 1993, 115, 10665; b) H.-G. Trauner, P. Le Floch, J. M. Le Four, L. Ricard, F. Mathey, Synthesis, 1995, 719; c) P. Rosa, P. Le Floch, L. Ricard, F. Mathey, J. Am. Chem. Soc. 1997, 119, 9417.
44. See for example: a) P. Le Floch, D. Carmichael, L. Ricard, F. Mathey, J. Am. Chem Soc. 1993, 115, 10665; b) H.-G. Trauner, P. Le Floch, J. M. Le Four, L. Ricard, F. Mathey, Synthesis, 1995, 719; c) P. Rosa, P. Le Floch, L. Ricard, F. Mathey, J. Am. Chem. Soc. 1997, 119, 9417.
45. See for example: a) P. Le Floch, D. Carmichael, L. Ricard, F. Mathey, J. Am. Chem Soc. 1993, 115, 10665; b) H.-G. Trauner, P. Le Floch, J. M. Le Four, L. Ricard, F. Mathey, Synthesis, 1995, 719; c) P. Rosa, P. Le Floch, L. Ricard, F. Mathey, J. Am. Chem. Soc. 1997, 119, 9417.
46. a) C. A. McAuliffe, in Comprehensive Coord. Chem. (Eds.: G. Wilkinson, R. D Gillard, J. A McCleverty), Pergamon, Oxford, 1982, 2, 989;
47. b) M. Pabel, S. B. Wild in Comprehensive Heterocyclic Chemistry II, Vol. 9 (Eds.: A R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, New York, 1996, 947.
48. a) F. Laporte, F. Mercier, L. Ricard, F. Mathey, J. Am Chem Soc. 1994, 116, 3306;
49. b) F. Mercier, F. Laporte, L Ricard, F. Mathey, M. Schröder, M. Regitz, Angew. Chem. 1997, 109, 2640; Angew. Chem. Int. Ed. Engl. 1997, 36, 2364
50. b) F. Mercier, F. Laporte, L Ricard, F. Mathey, M. Schröder, M. Regitz, Angew. Chem. 1997, 109, 2640; Angew. Chem. Int. Ed. Engl. 1997, 36, 2364
51. a) W Egan, R. Tang, G. Zon, K. Mislow, J. Am. Chem. Soc. 1970, 92, 1443;
52. b) W. Egan, R. Tang, G. Zon, K Mislow, J. Am. Chem. Soc. 1971, 93, 6205;
53. c) J. D. Andose, A. Rauk, K. Mislow, J. Am. Chem. Soc. 1974, 96, 6904;
54. d) A. N. Hughes, K. E. Edgecombe, Heterocycles, 1992, 33, 563;
55. e) D. B. Chesnut, L. D. Quin, J. Am. Chem. Soc. 1994, 116, 5779;
56. f) L Nyulaszi, J. Phys. Chem 1995, 99, 586;
57. g) A. Glukhotsev, A. Dransfeld, P. von R Schleyer, J. Phys Chem. 1996, 100, 13447;
58. h) L. Nyualszi, J. Phys. Chem. 1996, 100, 6194
59. a) N. Avarvari, P Le Floch, F. Mathey, J. Am. Chem. Soc. 1996, 118, 1978,
60. b) N. Avarvari, P. Le Floch, L. Ricard, F. Mathey, Organometallics, 1997, 16, 4089;
61. c) N. Mézailles, N. Avarvari, L. Ricard, F. Mathey, P. Le Floch, Inorg. Chem. 1998, 37, 5313.
62. N. Avarvari, N. Mézailles, L. Ricard, P Le Floch, F. Mathey, Science, 1998, 280, 1587.
63. M. Mascal, J. L. Richardson, A. Blake, W.-S. Li, Tetrahedron Lett. 1997, 38, 7639.
64. C. Wieser-Jeunesse, D. Matt, M. R. Yaftian, M. Burgard, J. Harrowfield, C. R. Acad. Sci. Ser. 2, 1998, 1, 479.
65. a) B. Konig, M. Rödel, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 107, 752; Angew. Chem. Int. Ed. Engl. 1995, 34, 661;
66. a) B. Konig, M. Rödel, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 107, 752; Angew. Chem. Int. Ed. Engl. 1995, 34, 661;
67. b) B. Konig, M. Rödel, P. Bubenitschek, P. G. Jones, I. Thondorf, J. Org. Chem. 1995, 60, 7406.
68. a) G. R. Newkome, Y. J. Joo, F. R. Fronczek, J Chem. Soc. Chem. Commun. 1987, 854;
69. b) R. M. Musau, A. Whiting, J. Chem. Soc. Chem. Commun. 1993, 1029;
70. c) R. M. Musau, A. Whiting, J. Chem. Soc. Perkin Trans. 1, 1994, 2881,
71. d) P. A. Gale, J. L. Sessler, V. Kral, V. Lynch, J. Am. Chem. Soc. 1996, 118, 5140;
72. e) J. Nakayama, N. Katano, Y. Sugihara, A. Ishii, Chem. Lett. 1997, 897;
73. f) P. A. Gale, J. L. Sessler, V. Kral, Chem. Commun. 1998, 1;
74. g) V. Kral, P. A. Gale, Jr. P. Anzenbacher, K. Jursikova, V. Lynch, J. L. Sessler, Chem. Commun. 1998, 9;
75. h) E. Vogel, C. Frode, A. Breihan, H. Schmickler, J. Lex, Angew. Chem. 1997, 109, 2722; Angew. Chem. Int. Ed. Engl. 1997, 36, 2609,
76. h) E. Vogel, C. Frode, A. Breihan, H. Schmickler, J. Lex, Angew. Chem. 1997, 109, 2722; Angew. Chem. Int. Ed. Engl. 1997, 36, 2609,
77. i) B. König, M. Rodel, Chem. Ber. 1997, 130, 421;
78. j) F. H. Carré, R. J P. Corriu, T. Deforth, W. E. Douglas, W. S. Siebert, W. Weinmann, Angew. Chem. 1998, 110, 654; Angew. Chem. Int Ed. 1998, 37, 652;
79. j) F. H. Carré, R. J P. Corriu, T. Deforth, W. E. Douglas, W. S. Siebert, W. Weinmann, Angew. Chem. 1998, 110, 654; Angew. Chem. Int Ed. 1998, 37, 652;
80. k) E. Vogel, J. Heterocycl. Chem 1996, 33, 1461.
81. M. E. Freeburger, L. Spialter, J. Org. Chem. 1970, 35, 652.
82. a) H. Lang, U. Lay, Z. Anorg. Allg. Chem. 1991, 596, 7;
83. b) B Wrackmeyer, G. Kehr, J. Suss, Chem. Ber. 1993, 126, 2221.
84. B. L. Feringa, R. Hulst, R. Rikers, Synthesis, 1998, 316.