Towards the synthesis of o-diphosphaquinones: Benzodiphosphadihydropentalene - Naphthodihydrodiphosphete

Liebigs Annales

Volumn , Issue 1, 1997, Pages 121-125

  Märkl, Gottfried ^a   Hennig, Rüdiger ^a   Nöth, Heinrich ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

DBU; Dihydrodiphosphete; Diphosphaquinone; Electrocyclization; Propargyl rearrangement

Indexed keywords

EID: 25544480295     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970118     Document Type: Article

References (45)

1. C. W. G. Fishwick, D. W. Jones in Chemistry of the Quinonoid Compounds, vol. II (Eds. S. Patai, Z. Rappoport), Wiley, Chichester, 1988, p. 403-454;
2. W. Oppolzer, Synthesis 1978, 793.
3. D. A. Ben-Efraim, F. Sondheimer, Tetrahedron Lett. 1963, 313;
4. C. M. Bowes, D. F. Montecalvo, F. Sondheimer, Tetrahedron Lett. ibid. 1973, 15, 3181;
5. F. W. Bell, C. M. Bowes, F. Sondheimer, Tetrahedron Lett. ibid. 1978, 20, 3299.
6. E. R. Brown in Chemistry of the Quinonoid Compounds, vol. II (Eds. S. Patai, Z. Rappoport), Wiley, Chichester 1988, p. 1231, and cited literature therein.
7. K. C. Raab, Dissertation, Universität Regensburg, 1990.
8. R. Appel in Multiple Bonds and Low Coordination in Phosphorus Chemistry, (Eds. M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, p. 157-219;
9. R. Appel, F. Knoll, I. Ruppert, Angew. Chem. 1981, 93, 771;
10. Angew. Chem., Int. Ed. Engl. 1981, 20, 732.
11. G. Märkl, K. C. Raab, R. Hennig, J. Chem. Soc., Chem. Commun., submitted.
12. R. Hennig, Dissertation, Universität Regensburg, 1994.
13. R. Appel, V. Winkhaus, F. Knoch, Chem. Ber. 1987, 120, 243;
14. G. Märkl, P. Kreitmeier, H. Nöth, K. Polborn, Angew. Chem. 1990, 102, 958;
15. Angew. Chem. Int. Ed. Engl. 1990, 29, 927;
16. K. Toyota, K. Tashiro, M. Yoshifuji, I. Miyahara, A. Hayashi, K. Hirotsu, J. Organomet. Chem. 1992, 431, C-3;
17. K. Toyota, K. Tashiro, M. Yoshifuji, Chem. Lett. 1991, 2079;
18. K. Toyota, K. Tashiro, M. Yoshifuji, S. Nagase, Bull. Chem. Soc. Jpn. 1992, 65, 2297;
19. K. Toyota, K. Tashiro, T. Abe, M. Yoshifuji, Heteroatom Chem. 1994, 5, 549;
20. G. Märkl, R. Hennig, Chem. Ber. submitted.
21. G. Märkl, R. Hennig, H. Nöth, Tetrahedron Lett. 1995, 36, 6429.
22. J.-C. Guillemin, T. Janati, J.-M. Denis, P. Guenot, P. Savignac, Tetrahedron Lett. 1994, 35, 245;
23. A.-C. Gaumont, J.-C. Guillemin, J.-M. Denis, J. Chem. Soc., Chem. Commun. 1994, 945.
24. G. Märkl, S. Reithinger, Tetrahedron Lett. 1988, 29, 463.
25. 3. Refinement in an orthorhombic space group provided no solution while refinement in the triclinic space group P1 led to a conventional R of 0.917 with the same problems for the disordered array of the annellated six- and five-membered C rings. Further details of the structure investigation are available from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-59287, the names of the authors, and the journal citation.
26. We could show that treatment of 13 with nBuLi gives 16 as one of the major products of a very complex mixture. The cyclization of 13 to 16 can be rationalized as follows. (Chemical Equation Presented)
27. 2 at -78°C. The assumption is supported by the fact, that the amount of naphthodihydrodiphosphete 17 did not increase by warming the NMR tube to -30°C.
28. F. Toda, K. Tanake, I. Sano, T. Isozaki, Angew. Chem. 1994, 106, 1856;
29. Angew. Chem. Int. Ed. Engl. 1994, 33, 1757.
30. P. Le Floch, N. Maigrot, L. Ricard, C. Charrier, F. Mathey, Inorg. Chem. 1995, 34, 5070;
31. G. Sillett, L. Ricard, C. Patois, F. Mathey, J. Am. Chem. Soc. 1992, 114, 9453.
32. N. Maigrot, C. Charrier, L. Ricard, F. Mathey, Polyhedron 1990, 9, 1363.
33. The mono- and bisdentate chromium, molybdenum and tungsten complexes of 1,4-bis(2,4,6-tri-tert-butylphenyl)-1,4-diphospha-1,3-butadiene (19) have been described by: R. Appel, B. Niemann, W. Schuhn, N. Siabalis, J. Organomet. Chem. 1988, 347, 299.
34. C. Grundmann in Methoden der Organischen Chemie (Houben-Weyl), Teil II (Ed. C. Grundmann), Thieme, Stuttgart, 1979, p. 1-186.
35. R. Appel, V. Barth, Tetrahedron Lett. 1980, 21, 1923;
36. R. Appel, V. Barth, F. Knoch, Chem. Ber. 1983, 116, 938.
37. C. Charrier, N. Maigrot, F. Mathey, F. Robert, Y. Jeannin, Organometallics 1986, 5, 623;
38. L. Ricard, N. Maigrot, C. Charrier, F. Mathey, Angew. Chem. 1987, 99, 590;
39. Angew. Chem. Int. Ed. Engl. 1987, 26, 548.
40. S. M. Bachrach, M. Liu, J. Org. Chem. 1992, 57, 2040.
41. R. Appel, J. Hünerbein, N. Siabalis, Angew. Chem. 1987, 99, 810;
42. Angew. Chem. Int. Ed. Engl. 1987, 26, 779.
43. S. Ito, K. Toyota, M. Yoshifuji, Chem. Lett. 1995, 747.
44. C. Huynh, G. Linstrumelle, Tetrahedron 1988, 44, 6337.
45. We thank Dr. T. Burgemeister and F. Kastner for carrying out the low-temperature NMR study.