Synthesis, structure, and reactivity of a 1σ4,3σ2-diphospaallene

Angewandte Chemie - International Edition

Volumn 39, Issue 18, 2000, Pages 3319-3321

  Kato, Tsuyoshi ^a   Gornitzka, Heinz ^a   Baceiredo, Antoine ^a   Bertrand, Guy ^a  

^a UMR 5069) 118 route de Narbonne   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; PHOSPHORANE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; PHOTOLYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034665612     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000915)39:18<3319::AID-ANIE3319>3.0.CO;2-M     Document Type: Article

References (35)

1. Reviews: a) Phosphorns Ylides (Ed.: O.I. Kolodiazhnyi), Wiley-VCH, Weinheim, 1999, pp. 186-198;
2. b) A. W. Johnson, W. C. Kaska, K. A. O. Starzewski, D. A. Dixon, Ylides and Imines of Phosphorus (Ed.: A.W. Johnson), Wiley-Interscience, New York, 1993, pp. 64-68;
3. c) H. J. Bestmann, R. Zimmermann, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, Vol. E1, 1982, pp. 752-758.
4. See for example: a) J. Escudié, H. Ranaivonjatovo, L. Rigon, Chem. Rev. 2000, in press;
5. b) M. Yoshifuji, K. Toyota, N. Inamoto, J. Chem. Soc. Chem. Commun. 1984, 689;
6. c) H. H. Karsch, H. U, Reisacher, G. Müller, Angew. Chem. 1984, 96, 621-623; Angew. Chem. Int. Ed. Engl. 1984, 23, 618-620;
7. c) H. H. Karsch, H. U, Reisacher, G. Müller, Angew. Chem. 1984, 96, 621-623; Angew. Chem. Int. Ed. Engl. 1984, 23, 618-620;
8. d) M. Gouygou, M. Koenig, J. Escudié, C. Couret, Heteroat. Chem. 1991, 2, 221-227.
9. H. P. Schrödel, G. Jochem, A. Schmidpeter, H. Nöth, Angew. Chem. 1995, 107, 2006-2010; Angew. Chem. Int. Ed. Engl. 1995, 34, 1853-1856.
10. H. P. Schrödel, G. Jochem, A. Schmidpeter, H. Nöth, Angew. Chem. 1995, 107, 2006-2010; Angew. Chem. Int. Ed. Engl. 1995, 34, 1853-1856.
11. D. Bourissou, G. Bertrand, Chem. Rev. 2000, 100, 39-91; F. Ford, T. Yuzawa, M. S. Platz, S. Matzinger, M. Fülscher, J. Am. Chem. Soc. 1998, 120, 4430-4438; H. M. Sulzbach, M. S. Platz, H. F. Schaefer III, C. M. Hadad, J. Am. Chem. Soc. 1997, 119, 5682-5689; A. E. Keating, M. A. Garcia-Garibay, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 10805-10809; W. Sander, G. Bucher, S. Wierlacher, Chem. Rev. 1993, 93, 1583-1621.
12. D. Bourissou, G. Bertrand, Chem. Rev. 2000, 100, 39-91; F. Ford, T. Yuzawa, M. S. Platz, S. Matzinger, M. Fülscher, J. Am. Chem. Soc. 1998, 120, 4430-4438; H. M. Sulzbach, M. S. Platz, H. F. Schaefer III, C. M. Hadad, J. Am. Chem. Soc. 1997, 119, 5682-5689; A. E. Keating, M. A. Garcia-Garibay, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 10805-10809; W. Sander, G. Bucher, S. Wierlacher, Chem. Rev. 1993, 93, 1583-1621.
13. D. Bourissou, G. Bertrand, Chem. Rev. 2000, 100, 39-91; F. Ford, T. Yuzawa, M. S. Platz, S. Matzinger, M. Fülscher, J. Am. Chem. Soc. 1998, 120, 4430-4438; H. M. Sulzbach, M. S. Platz, H. F. Schaefer III, C. M. Hadad, J. Am. Chem. Soc. 1997, 119, 5682-5689; A. E. Keating, M. A. Garcia-Garibay, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 10805-10809; W. Sander, G. Bucher, S. Wierlacher, Chem. Rev. 1993, 93, 1583-1621.
14. D. Bourissou, G. Bertrand, Chem. Rev. 2000, 100, 39-91; F. Ford, T. Yuzawa, M. S. Platz, S. Matzinger, M. Fülscher, J. Am. Chem. Soc. 1998, 120, 4430-4438; H. M. Sulzbach, M. S. Platz, H. F. Schaefer III, C. M. Hadad, J. Am. Chem. Soc. 1997, 119, 5682-5689; A. E. Keating, M. A. Garcia-Garibay, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 10805-10809; W. Sander, G. Bucher, S. Wierlacher, Chem. Rev. 1993, 93, 1583-1621.
15. D. Bourissou, G. Bertrand, Chem. Rev. 2000, 100, 39-91; F. Ford, T. Yuzawa, M. S. Platz, S. Matzinger, M. Fülscher, J. Am. Chem. Soc. 1998, 120, 4430-4438; H. M. Sulzbach, M. S. Platz, H. F. Schaefer III, C. M. Hadad, J. Am. Chem. Soc. 1997, 119, 5682-5689; A. E. Keating, M. A. Garcia-Garibay, K. N. Houk, J. Am. Chem. Soc. 1997, 119, 10805-10809; W. Sander, G. Bucher, S. Wierlacher, Chem. Rev. 1993, 93, 1583-1621.
16. A. Baceiredo, A. Igau, G. Bertrand, M. J. Menu, Y. Dartiguenave, J. J. Bonnet, J. Am. Chem. Soc. 1986, 108, 7868-7869.
17. O. I. Kolodiazhnyi, Russ. Chem. Rev. 1997, 66, 225-254; R. Appel, M. Huppertz, A. Westerhaus, Chem. Ber 1983, 116, 114-118.
18. O. I. Kolodiazhnyi, Russ. Chem. Rev. 1997, 66, 225-254; R. Appel, M. Huppertz, A. Westerhaus, Chem. Ber 1983, 116, 114-118.
19. M. Granier, A. Baceiredo, Y. Dartiguenave, M. Dartiguenave, M. J. Menu, G. Bertrand, J. Am. Chem. Soc. 1990, 112, 6277-6285.
20. CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data (Ed.: J. C. Tebby), CRC, Boca Raton, FL, 1991.
21. [2a] respectively.
22. 0.5; b) Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-144078 (2) and CCDC-144079 (5). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+ 44) 1223-336-033: e-mail: deposit@ccdc.cam.ac.uk).
23. R. Appel, Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer). Thieme, Stuttgart, 1990, pp. 157-219; L. N. Markovski, V.P. Romanenko, A. V. Ruban, Chemistry of Acyclic Compounds of Two-Coordinated Phosphorus. Naukova Dumka, Kiev, 1988.
24. R. Appel, Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer). Thieme, Stuttgart, 1990, pp. 157-219; L. N. Markovski, V.P. Romanenko, A. V. Ruban, Chemistry of Acyclic Compounds of Two-Coordinated Phosphorus. Naukova Dumka, Kiev, 1988.
25. P. von R. Schleyer, A. J. Kos, Tetrahedron 1983, 39, 1141-1150.
26. H. Grützmacher, H. Pritzkow, Angew. Chem. 1992, 104, 92-94; Angew. Chem. Int. Ed. Engl. 1992, 31, 99-101.
27. H. Grützmacher, H. Pritzkow, Angew. Chem. 1992, 104, 92-94; Angew. Chem. Int. Ed. Engl. 1992, 31, 99-101.
28. Phosphaalkenes with similar substituents have an E configuration because of the relative steric hindrance of the substituents: T. Kato, O. Polishchuk, H. Gornitzka, A. Baceiredo, G. Bertrand, J. Organomet. Chem. 2000, in press.
29. T. A. Van der Knaap, F. Bickelhaupt. Tetrahedron 1983, 39, 3189-3196.
30. J. M. Sotiropoulos, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1987, 109, 4711-4712.
31. Diazocumulene are usually highly unstable: D. Bourissou, G. Bertrand, C. R. Seances Acad. Sci. Paris 1996, 322, 489-506; J. C. Brahms, W. P. Dailey, J. Am. Chem. Soc. 1990, 112, 4046-4047.
32. Diazocumulene are usually highly unstable: D. Bourissou, G. Bertrand, C. R. Seances Acad. Sci. Paris 1996, 322, 489-506; J. C. Brahms, W. P. Dailey, J. Am. Chem. Soc. 1990, 112, 4046-4047.
33. C. Buron, H. Gornitzka, V. Romanenko, G. Bertrand. Science 2000, 288, 834-836.
34. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
35. SHELXL-97, Program for Crystal Structure Refinement, G. M. Sheldriek, University of Göttingen 1997.