[Cp2M] metallocene species promoted reductive coupling of Cl2C=PR: Synthesis, structure, and reactivity of the first 3,4-dihalo-1,2-dihydro-1,2-diphosphetes

Organometallics

Volumn 16, Issue 21, 1997, Pages 4551-4556

  Cénac, Nathalie ^a   Chrostowska, Anna ^b   Sotiropoulos, Jean Marc ^b   Donnadieu, Bruno ^a   Igau, Alain ^a   Pfister Guillouzo, Geneviève ^b   Majoral, Jean Pierre ^a  

^a CNRS   (France)

^b UNIVERSITÉ DE PAU ET DES PAYS DE L'ADOUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040008982     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970387n     Document Type: Article

References (50)

1. Dufour, N.; Caminade, A.-M.; Basso-Bert, M.; Igau, A.; Majoral, J.-P. Organometallics 1992, 11, 1131-7. Majorai, J.-P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879-86. Mahieu, A.; Miquel, Y.; Igau, A.; Donnadieu, B.; Majorai, J.-P. Unpublished results.
2. Dufour, N.; Caminade, A.-M.; Basso-Bert, M.; Igau, A.; Majoral, J.-P. Organometallics 1992, 11, 1131-7. Majorai, J.-P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879-86. Mahieu, A.; Miquel, Y.; Igau, A.; Donnadieu, B.; Majorai, J.-P. Unpublished results.
3. Dufour, N.; Caminade, A.-M.; Basso-Bert, M.; Igau, A.; Majoral, J.-P. Organometallics 1992, 11, 1131-7. Majorai, J.-P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879-86. Mahieu, A.; Miquel, Y.; Igau, A.; Donnadieu, B.; Majorai, J.-P. Unpublished results.
4. Igau, A.; Dufour, N.; Mahieu, A.; Majorai, J. P. Angew. Chem., Int. Ed. Engl. 1993, 32, 95. Mahieu, A.; Igau, A.; Jaud, J.; Majoral, J. P. Organometallics 1995, 14, 944-52.
5. Igau, A.; Dufour, N.; Mahieu, A.; Majorai, J. P. Angew. Chem., Int. Ed. Engl. 1993, 32, 95. Mahieu, A.; Igau, A.; Jaud, J.; Majoral, J. P. Organometallics 1995, 14, 944-52.
6. Negishi, E.-I. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163.
7. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arnd, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-7. Hansawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299-305.
8. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arnd, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-7. Hansawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299-305.
9. For the preparation of 1,2-dihydro-1,2-diphosphetes, see, for example: Charrier, C.; Maigrot, N.; Mathey, F.; Robert, F.; Jeannin, Y. Organometallics 1986, 5, 623-30. Ricard, L.; Maigrot, N.; Charrier, C.; Mathey, F. Angew. Chem. 1987, 99, 590; Angew. Chem., Int. Ed. Engl. 1987, 26, 548-9 and references therein.
10. For the preparation of 1,2-dihydro-1,2-diphosphetes, see, for example: Charrier, C.; Maigrot, N.; Mathey, F.; Robert, F.; Jeannin, Y. Organometallics 1986, 5, 623-30. Ricard, L.; Maigrot, N.; Charrier, C.; Mathey, F. Angew. Chem. 1987, 99, 590; Angew. Chem., Int. Ed. Engl. 1987, 26, 548-9 and references therein.
11. For the preparation of 1,2-dihydro-1,2-diphosphetes, see, for example: Charrier, C.; Maigrot, N.; Mathey, F.; Robert, F.; Jeannin, Y. Organometallics 1986, 5, 623-30. Ricard, L.; Maigrot, N.; Charrier, C.; Mathey, F. Angew. Chem. 1987, 99, 590; Angew. Chem., Int. Ed. Engl. 1987, 26, 548-9 and references therein.
12. Fachinetti, G.; Floriani, C.; Marchetti, F.; Mellini, M. J. Chem. Soc., Dalton Trans. 1978, 1398.
13. Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. S.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
14. Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. S.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
15. 1H} -103.7 ppm) was observed. Markovskii, L. N.; Koidan, G. N.; Marchenko, A. P.; Romanenko, V. D.; PovolotskiiI, M. I.; Pinchuk, A. M. Zh. Obshch. Khim. 1989, 59, 2133.
16. Niecke, E.; Fuchs, A.; Baumeister, F.; Nieger, M.; Schoeller, W. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 555-7.
17. (a) Charrier, C.; Guilhem, J.; Mathey, F. J. Org. Chem. 1981, 46, 3-8.
18. (b) Becker, G.; Becker, W.; Uhl, G. Z. Anorg. Allg. Chem. 1984, 519, 31-41.
19. (c) Charrier, C.; Maigrot, N.; Mathey, F.; Robert, F.; Jeanin, Y. Organometallics 1986, 5, 623-30.
20. (d) Philips, I. G.; Ball, R. G.; Cavell, R. G. Inorg. Chem. 1988, 27, 2269-75.
21. (e) Maigrot, N.; Charrier, C.; Ricard, L.; F. Mathey, F. Polyhedron 1990, 9, 1363-7.
22. (f) Binger, P.; Wettling, T.; Schneider, R.; Zurmühlen, F.; Bergsträsser, U.; Hoffmann, J.; Maas, G.; Regitz, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 207.
23. (g) Geissler, B.; Barth, S.; Bergsträsser, U.; Slany, M.; Durkin, J.; Hitchcock, P. B.; Hofmann, M.; Binger, P.; Nixon, J. F.; von R. Schleyer, P.; Regitz, M. Ibid. 1995, 34, 484-7.
24. (h) Knoch, F.; Kummer, S.; Zenneck, U. Synthesis 1996, 265-8.
25. The P-P bond lengths in bis(dialkylamino)diphosphines are 2.250 Å. For examples, see: Bender, H. R. G.; Niecke, E.; Nieger, M.; Westermann, H. Z. Anorg. Allg. Chem. 1994, 620, 1194-202.
26. 2 are 2.236 and 2.235 Å, respectively.
27. Foster, J. P.; Weinhold, F. J. J. Am. Chem. Soc. 1980, 102, 7211-8. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735-46. Reed, A. E.; Weinhold, F. J. Ibid. 1985, 83, 1736-40.
28. Foster, J. P.; Weinhold, F. J. J. Am. Chem. Soc. 1980, 102, 7211-8. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735-46. Reed, A. E.; Weinhold, F. J. Ibid. 1985, 83, 1736-40.
29. Foster, J. P.; Weinhold, F. J. J. Am. Chem. Soc. 1980, 102, 7211-8. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735-46. Reed, A. E.; Weinhold, F. J. Ibid. 1985, 83, 1736-40.
30. Reed, A. E.; Curtiss, L. A.; Weinhold, F. J. J. Chem. Rev. 1988, 88, 899-926.
31. Van der Knaap, Th. A.; Klebach, Th. C.; Visser, F.; Bickelhaupt, F.; Ros, P.; Baerends, E. J.; Stam, C. H.; Konijn, M. Tetrahedron 1984, 40, 765-76.
32. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazuki, T.; Iwata, S. Handbook of He I photoelectron spectra of fundamental organic molecules; Japan Scientific Societies Press, Halsted Press: New York, 1981.
33. Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729-42.
34. Jun, H.; Angelici, R. J. Organometallics 1993, 12, 4265-6 and references therein.
35. Le Floch, P.; Kolb, A.; Mathey, F. J. Chem. Soc., Chem. Commun. 1994, 2065-6.
36. For the reactivity of (phosphaalkenyl)metal species see, for example: Van der Sluis, M.; Wit, J. B. M.; Bickelhaupt, F. Organometallics 1996, 15, 174-80 and references therein.
37. 4 derivatives in general. Barach, S. M.; Liu, M. J. Org. Chem. 1992, 57, 2040-7 and ref 9.
38. Negishi, E.; Cedermabaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
39. Sikora, D. J.; Moriarty, K. J.; Rausch, M. D. Inorg. Synth. 1990, 28, 248.
40. Prishchenko, A. A.; Gromov, A. V.; Lutsenko, I. F. Zh. Obshch. Khim. 1984, 54, 1520.
41. Koidan, G. N.; Olenik, V. A.; Marchenko, A. P.; Pinchuk, A. M. Zh. Obshch. Khim. 1988, 58, 1923.
42. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Reploge, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92; Gaussian Inc.: Pittsburgh, PA, 1992.
43. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
44. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
45. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
46. Walker, N.; Stuart, D. Acta Crystallogr. 1983, 39, 158.
47. Watkin, D. J.; Prout, C. K.; Carruthers, R. J.; Betteridge, P. CRYSTALS. Chemical Crystallography Laboratory: Oxford, U.K., 1996; Issue 10.
48. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England; Vol. IV.
49. Sheldrick, G. M. SHELXS 86, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1986.
50. Further details of the crystal structure determination can be ordered from Fachinformations-zentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen, under the depository number CSD-406167 for 2a.