Thermal Rearrangement of 1,5,8-Triphosphaisolumibullvalenes (1,5,8-Triphosphatetracyclo[4.4.0.02,8.0 5,7]deca-3,9-dienes)

European Journal of Organic Chemistry

Volumn , Issue 21, 2003, Pages 4292-4300

  Disteldorf, Hendrik ^a   Renner, Jens ^a   Heydt, Heinrich ^a   Binger, Paul ^a   Regitz, Manfred ^a  

^a University of Koblenz Landau   (Germany)

Author keywords

Alkyne complexes; Heterocycles; Phosphorus carbon cage compounds; Rearrangements

Indexed keywords

1,1B,2A TRIPHOSPHAHOMOQUADRICYCLANE DERIVATIVE; 1,5,8 TRIPHOSPHAISOLUMIBULLVALENE DERIVATIVE; 1,5,8 TRIPHOSPHATETRACYCLO[4.4.0.0 2,8.0 5,7]DECA 3,9 DIENE DERIVATIVE; ALKADIENE; ALKANE DERIVATIVE; TETRAHYDRO 1H 1,1B,2A TRIPHOSPHADICYCLOPROPA[CD,GH]PENTALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE SENSITIVITY; THERMAL ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0242595727     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300173     Document Type: Article

References (34)

1. For Part 169, see: J. Renner, U. Bergsträßer, P. Binger, M. Regitz, Angew. Chem. Int. Ed. 2003, 42, 1863-1866.
2. A. T. Balaban, M. Banciu, J. Chem. Educ. 1984, 61, 766-769.
3. [31 [3a] H. Hopf, in: Classics in Hydrocarbon Chemistry, Wiley-VCH, 2000, p. 220.
4. [3b] J. J. Gajewski, in: Hydrocarbon Thermal Isomerizations, John Wiley & Sons, New York, 1981, pp. 343-365.
5. For nomenclature, see: ref. [3b], p. 350.
6. M. Jones Jr., S. D. Reich, L. T. Scott, J. Am. Chem. Soc. 1970, 92, 3118-3126.
7. G. Maier, N. H. Wiegand, S. Baum, R. Wuellner, Chem. Ber. 1989, 122, 781-794.
8. For a review on the chemistry of 1,3,5-triphosphinines, see: H. Heydt, Top. Curr. Chem. 2003, 223, 216-249.
9. C. Peters, S. Stutzmann, H. Disteldorf, S. Werner, U. Bergsträßer, C. Krüger, P. Binger, M. Regitz, Synthesis 2000, 529-536.
10. H. E. Zimmerman, G. L. Grunewald, J. Am. Chem. Soc. 1964, 86, 1434.
11. For reviews on the chemistry of phosphorus/carbon cage compounds, see: [10a] M. Regitz, A. Hoffmann, U. Bergsträßer, in: Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, New York, 1995, pp. 173-201.
12. [10b] A. Mack, M. Regitz, in: Carbocyclic and Heterocyclic Cage Compounds and their Building Blocks (Ed.: K. K. Laali), Supplement 1 of the series Advances in Strained and Interesting Organic Molecules (Ed.: B. Halton), JAI Press Inc, Stamford, 1999, pp. 199-221.
13. [11a] F. Tabellion, A. Nachbauer, S. Leininger, C. Peters, M. Regitz, F. Preuss, Angew. Chem. Int. Ed. 1998, 37, 1233-1235.
14. [11b] F. Tabellion, C. Peters, U. Fischbeck, M. Regitz, F. Preuss, Chem. Eur. J. 2000, 6, 4558-4566.
15. F. Mathey, Chem. Rev. 1990, 90, 997.
16. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
17. [14a] B. Breit, U. Bergsträßer, G. Maas, M. Regitz, Angew. Chem. Int. Ed. Engl. 1992, 31, 1055.
18. [14b] P. Binger, K. Günther, M. Regitz, Synthesis 1999, 1363.
19. [14c] C. Peters, H. Disteldorf, E. Fuchs, S. Werner, S. Stutzmann, J. Bruckmann, C. Krüger, P. Binger, H. Heydt, M. Regitz, Eur. J. Org. Chem. 2001, 3425.
20. [15a] H. Prinzbach, H.-D. Martin, Helv. Chim. Acta 1968, 51, 438.
21. [15b] P. Sargeant, J. Am. Chem. Soc. 1969, 91, 3061.
22. [15c] D. T. Longone, D. M. Stehower, Tetrahedron Lett. 1970, 1017.
23. K. Hassenrück, H.-D. Martin, B. Mayer, T. Urbanek, T. Zirwes, R. Walsh, H.-D. Beckhaus, Chem. Ber. 1987, 120, 177-186.
24. [17a] H. Prinzbach, W. Eberbach, M. Klaus, G. v. Veh, Chem. Ber. 1968, 101, 4066.
25. [17b] R. B. Kinnel, P. K. Freeman, Terahedron Lett. 1973, 4803.
26. C. W. Jefford, J. Mareda, J.-C. E. Gehret, T. Kabengele, W. D. Graham, U. Burger, J. Am. Chem. Soc. 1976, 98, 2585.
27. P. J. Stang, in: Methoden Org. Chem. (Houben-Weyl) (Ed.: M. Regitz), 4th Ed., E19b, Thieme, Stuttgart, 1989, p. 84-135.
28. S. Aime, L. Milone, R. Rossetti, P. L. Stanghellini, Inorg. Chim. Acta 1977, 22, 135.
29. J. Chauvelier, F. Bardone, Bull. Soc. Chim. Fr. 1952, 386.
30. S. Takahashi, K. Kuroyama, K., Sonogashira, N. Hagihara, Synthesis 1980, 627.
31. W. P. Jackson, Synlett 1990, 536.
32. G. M. Sheldrick, SHELXS-86 Fortran Program for the Solution of Crystal Structures from Diffraction Data, Institute for Organic Chemistry, University of Göttingen, 1990.
33. G. M. Shedrick, SHELXL-93 Fortran Program for Crystal Structure Refinement, Institute for Organic Chemistry, University of Göttingen, 1993.
34. Crystallographic data (excluding structure factors) for the structure 6d have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-220258. Copies of the data can be obtained free of charge on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) +44-1223-336-033, E-mail: deposit@ccdc.cam.ac.uk].