1,2,3-Triphosphetenes, first examples of a new class of phosphorus heterocycles

Chemistry - A European Journal

Volumn 2, Issue 2, 1996, Pages 208-213

  Pucknat, Heike ^a   Grobe, Joseph ^a   Le Van, Duc ^a   Broschk, Burkhardt ^a   Hegemann, Marianne ^a   Krebs, Bernt ^a   Läge, Mechtild ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Heterocycles; Insertion reactions; Phosphaalkynes; Phosphorus ylides; Triphosphetenes

Indexed keywords

HETEROCYCLES; INSERTION REACTIONS; PHOSPHAALKYNES; PHOSPHORUS YLIDES; TRIPHOSPHETENES;

X RAY DIFFRACTION;

PHOSPHORUS;

EID: 0010832859     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020213     Document Type: Article

References (69)

1. T. Albers, J. Grobe, D. Le Van, B. Krebs, M. Läge, Z. Naturforsch. 1995, 50b, 94-100.
2. M. Baudler, D. Düster, D. Ouzounis, Z. Anorg. Allg. Chem. 1987, 544, 87-94.
3. Intramolecular [2+2]-cycloaddition of 1,2,4-triphosphabuta-1,3-dienes does not yield II but 1,2,3-triphosphabicyclobutanes: a) R. Appel, B. Niemann, M. Nieger, Angew. Chem. 1988, 100, 957-958;
4. Angew. Chem. Int. Ed. Engl. 1988, 27, 957-958;
5. b) E. Niecke, O. Almeyer, M. Nieger, J. Chem. Soc. Chem. Commun. 1988, 945-946.
6. a) E. Fluck, B. Neumüller in Rings, Clusters and Polymers of Main Group and Transition Elements (Ed.: H. W. Roesky), Elsevier, Amsterdam, 1989, pp. 195-305;
7. b) In a recent review, a coordinated 1,2,3-triphosphacyclobutadiene derivative was mentioned but without any details: P. Binger in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, pp. 90-111.
8. M. Regitz, P. Binger, Angew. Chem. 1988, 100, 1541-1565;
9. Angew. Chem. Int. Ed. Engl. 1988, 27, 1484-1508;
10. see also: M. Regitz, P. Binger in ref. [4b], pp. 58-111.
11. B. Breit, U. Bergsträsser, G. Maas, M. Regitz, Angew. Chem. 1992, 104, 1043-1046;
12. Angew. Chem. Int. Ed. Engl. 1992, 31, 1055-1058.
13. R. Streubel, M. Frost, M. Nieger, E. Niecke, Bull. Soc. Chim. Fr. 1993, 130, 642-646.
14. B. Breit, M. Regitz, Chem. Ber. 1993, 126, 1945-1950.
15. J. Grobe, A. Armbrecht, T. Grosspietsch, M. Hegemann, D. Le Van, Phosphorus Sulfur Silicon, 1993, 77, 245.
16. B. Breit, R. Boese, M. Regitz, J. Organomet. Chem. 1994, 464, 41-45.
17. W. Mahler, J. Am. Chem. Soc. 1964, 86, 2306-2307.
18. U. Schmidt, Angew. Chem. 1975, 87, 535-540;
19. Angew. Chem. Int. Ed. Engl. 1975, 14, 523-528.
20. a) C. Charrier, J. Guilhem, F. Mathey, J. Org. Chem. 1981, 46, 3-8;
21. b) C. Charrier, N. Maigrot, F. Mathey, F. Robert, Y. Jeannin, Organometallics 1986, 5, 623-630.
22. I. G. Phillips, R. G. Ball, R. G. Cavell, Inorg. Chem. 1988, 27, 2269-2275.
23. A. Karst, J. Grobe, D. Le Van, B. Broschk, Z. Naturforsch., 1995, 50b, 189-195.
24. a) R. Appel, U. Kündgen, F. Knoch, Chem. Ber. 1985, 118, 1352-1370;
25. b) V. D. Romanenko, T. V. Sarina, M. I. Povolotskii, L. N. Markovskii, Zh. Obshch. Khim. 1985, 55, 1437-1438.
26. R. Appel, V. Barth, F. Knoch, Chem. Ber. 1983, 116, 938-950;
27. R. Appel, F. Knoch, B. Laubach, R. Sievers, ibid. 1983, 116, 1873-1879.
28. H. Borrmann, I. Kovacs, G. Fritz, Z. Anorg. Allg. Chem. 1994, 620, 1818-1820.
29. E. Niecke, R. Streubel, M. Nieger, D. Stalke, Angew. Chem. 1989, 101, 1708-1710;
30. Angew. Chem. Int. Ed. Engl. 1989, 28, 1673-1674.
31. G. Becker, M. Böhringer, R. Gleiter, K. H. Pfeifer, J. Grobe, D. Le Van, M. Hegemann, Chem. Ber. 1994, 127, 1041-1045.
32. J. Grobe, D. Le Van, M. Hegemann, B. Krebs, M. Läge, Angew. Chem. 1992, 104, 94-96;
33. Angew. Chem. Int. Ed. Engl. 1992, 31, 95-97;
34. Chem. Ber. 1992, 125, 411-414;
35. ibid. 1993, 126, 63-65;
36. Heteroat. Chem. 1994, 5, 337-341.
37. G. Fritz, T. Vaahs, H. Fleischer, E. Matern, Angew. Chem. 1989, 101, 324-325;
38. Angew. Chem. Int. Ed. Engl. 1989, 29, 315-316;
39. Z. Anorg. Allg. Chem. 1989, 570, 54-66.
40. J. Grobe, D. Le Van, J. Schulze, Z. Naturforsch. 1985, 40b, 1753-1755;
41. J. Grobe, T. Grosspietsch, D. Le Van, J. Schulze, B. Krebs, M. Dartmann, J. Organomet. Chem. 1990, 385, 255-275;
42. J. Grobe, D. Le Van, S. Martin, Z. Anorg. Allg. Chem. 1989, 579, 35-46.
43. A. B. Burg, W. Mahler, J. Am. Chem. Soc. 1961, 83, 2388-2389;
44. A. H. Cowley, M. C. Cushner, Inorg. Chem. 1980, 19, 515-518.
45. A. H. Cowley, J. Organomet. Chem. 1990, 400, 71-80;
46. L. R. Avens, R. A. Wolcott, L. V. Cribbs, J. L. Mills, Inorg. Chem. 1989, 28, 200-205.
47. D. Le Van, J. Grobe, unpublished results.
48. D. C. Burton, D. G. Naae, R. M. Flynn, B. E. Smart, D. R. Brittelie, J. Org. Chem. 1983, 48, 3616-3618;
49. see also: J. Grobe, D. Le Van, J. Nientiedt, New J. Chem. 1989, 13, 363-367.
50. H. J. Bestmann, A. J. Kos, K. Witzgall, P. von R. Schleyer, Chem. Ber. 1986, 119, 1331-1349.
51. a) D. G. Gilheany in The Chemistry of Organophosphorus Compounds (Ed.: F. R. Hartley), John Wiley, 1994, Vol. 3, 1-44;
52. 2) distance of 1.79 Å was observed for the 2-phosphonio-substituted 1-phosphaalkene: H. Grützmacher, H. Pritzkow, Angew. Chem. 1989, 101, 768-769;
53. Angew. Chem. Int. Ed. Engl. 1989, 28, 740-741.
54. H. Schmidbaur, J. Jeong, A. Schier, W. Graf, D. L. Wilkinson, G. Müller, C. Krüger, New J. Chem. 1989, 13, 341-352.
55. G. J. Palenik, J. Donahue, Acta Crystallogr. 1962, 15, 564-569.
56. M. Baudler, J. Hellmann, P. Bachmann, K.-F. Tebbe, R. Fröhlich, M. Fehér, Angew. Chem. 1981, 93, 415-417;
57. Angew. Chem. Int. Ed. Engl. 1981, 20, 406-407.
58. C. Schade, P. von R. Schleyer, J. Chem. Soc. Chem. Commun. 1987, 1399-1401.
59. L. Pauling, Die Natur der chemischen Bindung, 3rd ed., Verlag Chemie, Weinheim, 1976, p. 217.
60. M. A. Howells, R. D. Howells, N. C. Baenziger, D. J. Burton, J. Am. Chem. Soc. 1973, 95, 5366-5370.
61. H. Schmidbaur, A. Schier, C. M. F. Frazão, G. Müller, J. Am. Chem. Soc. 1986, 108, 976-982.
62. J. Grobe, D. Le Van, B. Lüth, M. Hegemann, Chem. Ber. 1990, 123, 2317-2320.
63. G. Becker, G. Gresser, W. Uhl, Z. Naturforsch. 1981, 36b, 16-19;
64. G. Becker, H. Schmidt, G. Uhl, W. Uhl, Inorg. Synth. 1990, 27, 249-253.
65. W. Rösch, U. Vogelbacher, T. Allspach, M. Regitz, J. Organomet. Chem. 1986, 306, 39-53;
66. M. Regitz, W. Rösch, T. Allspach, U. Annen, K. Blatter, J. Fink, M. Hermesdorf, H. Heydt, U. Vogelbacher, O. Wagner, Phosphorus Sulfur 1987, 30, 479-482.
67. W. Mahler, A. B. Burg, J. Am. Chem. Soc. 1958, 80, 6161-6167.
68. Further details of the crystal structure investigation may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-58975.
69. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Determination, University of Göttingen, 1993.