Syntheses of 2H-1,3,2-diazaphosphole, 2H-1,4,2-diazaphosphole, and Δ3-1,3,2-oxazaphospholene complexes; first examples of 2H-azaphosphirene complex formation by [2+1] cycloaddition

Chemistry - A European Journal

Volumn 4, Issue 8, 1998, Pages 1542-1553

  Wilkens, Hendrik ^a   Ruthe, Frank ^a   Jones, Peter G ^a   Streubel, Rainer ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

2H azaphosphirene complexes; Cycloadditions; Phosphorus heterocycles; Tungsten

Indexed keywords

EID: 0031858395     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980807)4:8<1542::AID-CHEM1542>3.0.CO;2-X     Document Type: Article

References (63)

1. R. Streubel, A. Ostrowski, S. Priemer, U. Rohde, J. Jeske, P. G. Jones, Eur. J. Inorg. Chem. 1998, 257-261.
2. For reviews on 2H-azirenes (or 2H-azirines), see: a) A. Padwa, Acc. Chem. Res. 1976, 9, 371-378; b) V. Nair, K. H. Kim, Heterocycles 1977, 7, 353; b) H. J. Hansen, H. Heimgartner in 1,3-Dipolar Cycloaddition Chemistry, (Ed.; A. Padwa), Wiley, New York, 1984, ch. 2, pp. 177-290.
3. For reviews on 2H-azirenes (or 2H-azirines), see: a) A. Padwa, Acc. Chem. Res. 1976, 9, 371-378; b) V. Nair, K. H. Kim, Heterocycles 1977, 7, 353; b) H. J. Hansen, H. Heimgartner in 1,3-Dipolar Cycloaddition Chemistry, (Ed.; A. Padwa), Wiley, New York, 1984, ch. 2, pp. 177-290.
4. For reviews on 2H-azirenes (or 2H-azirines), see: a) A. Padwa, Acc. Chem. Res. 1976, 9, 371-378; b) V. Nair, K. H. Kim, Heterocycles 1977, 7, 353; b) H. J. Hansen, H. Heimgartner in 1,3-Dipolar Cycloaddition Chemistry, (Ed.; A. Padwa), Wiley, New York, 1984, ch. 2, pp. 177-290.
5. a) M. Granier, A. Baceiredo, H.-J. Grützmacher, H. Pritzkow, G. Bertrand, Angew. Chem. 1990, 102, 671-672; Angew. Chem. Int. Ed. Engl. 1990, 29, 659-660;
6. a) M. Granier, A. Baceiredo, H.-J. Grützmacher, H. Pritzkow, G. Bertrand, Angew. Chem. 1990, 102, 671-672; Angew. Chem. Int. Ed. Engl. 1990, 29, 659-660;
7. b) N. Dubau-Assibat, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1996, 118, 5216-5220.
8. For a review on nitrile ylides, see: a) P. K. Claus in Houben-Weyl, Meth. Org. Chem., Bd. E 14b (1), 1990, pp. 1-33, and references therein.
9. For reviews on nitrile imines, see: a) P. K. Claus in Houben-Weyl, Meth. Org. Chem., Bd. E 14b (1), 1990, pp. 33-73; b) G. Bertrand, C. Wentrup, Angew. Chem. 1994, 106, 529-548; Angew. Chem Int. Ed. Engl. 1994, 33, 527-546, and references therein.
10. For reviews on nitrile imines, see: a) P. K. Claus in Houben-Weyl, Meth. Org. Chem., Bd. E 14b (1), 1990, pp. 33-73; b) G. Bertrand, C. Wentrup, Angew. Chem. 1994, 106, 529-548; Angew. Chem Int. Ed. Engl. 1994, 33, 527-546, and references therein.
11. For reviews on nitrile imines, see: a) P. K. Claus in Houben-Weyl, Meth. Org. Chem., Bd. E 14b (1), 1990, pp. 33-73; b) G. Bertrand, C. Wentrup, Angew. Chem. 1994, 106, 529-548; Angew. Chem Int. Ed. Engl. 1994, 33, 527-546, and references therein.
12. a) G. Alcaraz, U. Wecker, A. Baceiredo, G. Bertrand, Angew. Chem. 1995, 107, 1358-1359; Angew. Chem. Int. Ed. Eng. 1995, 34, 1246-1247;
13. a) G. Alcaraz, U. Wecker, A. Baceiredo, G. Bertrand, Angew. Chem. 1995, 107, 1358-1359; Angew. Chem. Int. Ed. Eng. 1995, 34, 1246-1247;
14. b) V. Piquet, A. Baceiredo, H. Gornitzka, F. Dahan, G. Bertrand, Chem. Eur. J. 1997, 3, 1757-1764.
15. For a review on phosphinidenes and electrophilic terminal phosphanediyl complexes, see: F. Mathey, Angew. Chem. 1987, 99, 285-296; Angew. Chem. Int. Ed. Engl. 1987, 26, 275-285.
16. For a review on phosphinidenes and electrophilic terminal phosphanediyl complexes, see: F. Mathey, Angew. Chem. 1987, 99, 285-296; Angew. Chem. Int. Ed. Engl. 1987, 26, 275-285.
17. For transiently formed 2H-azasilirenes, see: a) M. Weidenbruch, A. Schäfer, J. Organomet. Chem. 1986, 314, 25-32; b) M. Weidenbruch, P. Will, Z. Anorg. Allg. Chem. 1996, 622, 1811-1813.
18. For transiently formed 2H-azasilirenes, see: a) M. Weidenbruch, A. Schäfer, J. Organomet. Chem. 1986, 314, 25-32; b) M. Weidenbruch, P. Will, Z. Anorg. Allg. Chem. 1996, 622, 1811-1813.
19. a) R. Okazaki, H. Suzuki, N. Tokitoh, Xth International Symposium on Organosilicon Chemistry, Montpellier, France, 1996, poster abstract 60;
20. b) R. Okazaki, R. West in Multiply Bonded Main Group Metals and Metalloids, (Eds.: R. West, F. G. A. Stone). Academic Press, London. 1996, pp. 232-270.
21. For a review on transiently formed 1H-diazirenes, see: X. Creary, Acc. Chem. Res. 1992, 25, 31-38.
22. G. Alcaraz, V. Piquet, A. Baceiredo, F. Dahan, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 1996, 118, 1060-1065.
23. a) S. Fischer, C. Wentrup, J. Chem. Soc. Chem. Commun. 1980, 502-503.
24. R. Streubel, J. Jeske, P. G. Jones, R. Herbst-Irmer, Angew. Chem. 1994, 106, 115-117; Angew. Chem. Int. Ed. Engl. 1994, 33, 80-82.
25. R. Streubel, J. Jeske, P. G. Jones, R. Herbst-Irmer, Angew. Chem. 1994, 106, 115-117; Angew. Chem. Int. Ed. Engl. 1994, 33, 80-82.
26. R. Streubel, H. Wilkens, A. Ostrowski, C. Neumann, F. Ruthe, P. G. Jones, Angew. Chem. 1997, 109, 1549-1550; Int. Ed. Engl. 1997, 36, 1492-1493.
27. R. Streubel, H. Wilkens, A. Ostrowski, C. Neumann, F. Ruthe, P. G. Jones, Angew. Chem. 1997, 109, 1549-1550; Int. Ed. Engl. 1997, 36, 1492-1493.
28. H. Wilkens, J. Jeske, P. G. Jones, R. Streubel, Chem. Commun. 1997, 2317-2318.
29. R. Streubel, A. Ostrowski, H. Wilkens, F. Ruthe, J. Jeske, P. G. Jones, Angew. Chem. 1997, 109, 409-413; Angew. Chem. Int. Ed. Engl. 1997, 36, 378-381.
30. R. Streubel, A. Ostrowski, H. Wilkens, F. Ruthe, J. Jeske, P. G. Jones, Angew. Chem. 1997, 109, 409-413; Angew. Chem. Int. Ed. Engl. 1997, 36, 378-381.
31. For a review on nitrile sulfides, see: R. M. Paton, Chem. Soc. Rev. 1989, 18, 33-52.
32. a) A. Ostrowski, J. Jeske, P. G. Jones, J. Chem. Soc. Chem. Commun. 1995, 2113-2114;
33. b) A. Ostrowski, J. Jeske, F. Ruthe, P. G. Jones, R. Streubel, Z. Anorg. Allg. Chem. 1997, 623, 1897-1902.
34. R. Streubel, L. Ernst, J. Jeske, P. G. Jones, J. Chem. Soc. Chem. Commun. 1995, 2113-2114.
35. R. Streubel. unpublished results.
36. R. K. Howe, J. E. Franz, J. Org. Chem. 1974, 39, 962-964.
37. W. Stegmann, P. Uebelhart, H. Heimgartner, Helv. Chim. Acta 1983, 66, 2254-2268.
38. R. Streubel, S. Priemer, F. Ruthe, P. G. Jones, D. Gudat, Eur. J. Inorg. Chem. 1998, 575-578.
39. J. Mason, Multinuclear NMR, Plenum Press, New York, 1987.
40. a) H. Giezendanner, H. Heimgartner, B. Jackson, T. Winkler, H.-J. Hansen, H. Schmid, Helv. 1973, 56, 2611-2627;
41. b) N. Gakis, H. Heimgartner, H. Schmid, ibid 1975, 58, 749-760;
42. c) P. Gilgen, H.-J. Hansen, H. Heimgartner, W. Sieber, P. Uebelhart, H. Schmid, P. Schönholzer, W. Oberhänsli, ibid 1975, 58, 1739-1768.
43. a) J. Luber, A. Schmidpeter, Chem. Ztg. 1976, 100, 392-393;
44. b) Y. G. Gololobov, Y. V. Balizky, Rev. Heteroat. Chem. 1992, 6, 25-75.
45. A. H. Cowley, S. W. Hall, R. A. Jones, C. M. Nunn, J. Chem. Soc. Chem. Commun. 1988, 867-868.
46. W. Stegmann, P. Gilgen, H. Heimgartner, H. Schmid. Helv. 1976, 59, 1018-1027.
47. K. Burger, K. Einhellig, Chem. Ber. 1973, 106, 3421-3430.
48. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-101151. 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).
49. F. A. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. II 1987, S1-S19.
50. P. B. Hitchcock, P. L. Pye, J. Chem. Soc. Dalton Trans. II 1977, 1457-1460.
51. a) P. Caramella, K. N. Houk, J. Am. Chem. Soc. 1976, 98, 6397-6398;
52. b) K. N. Houk, Top. Curr. Chem., New York, 1979, 79, 1-40.
53. R. Sustmann, Pure Appl. Chem. 1975, 40, 569-593.
54. a) A. Padwa, P. H. J. Carlson, J. Am. Chem. Soc. 1975, 97, 3862-3864;
55. b) A. Padwa, A. Ku, A. Mazzu, S. I. Wetmore Jr., J. Am. Chem. Soc. 1976, 98, 1048-1050;
56. c) A. Padwa, S. Hornbuckle, Chem. Rev. 1991, 97, 263-309.
57. a) A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363;
58. b) R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211-1213; Angew. Chem. Int. Ed. Engl. 1997, 35, 1121-1122;
59. b) R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211-1213; Angew. Chem. Int. Ed. Engl. 1997, 35, 1121-1122;
60. c) M. K. Denk, A. Thadani, K. Hatano, A. J. Lough, Angew. Chem. 1997, 109, 2719-2721; Angew. Chem. Int. Ed. Engl. 1997, 36, 2607-2609;
61. c) M. K. Denk, A. Thadani, K. Hatano, A. J. Lough, Angew. Chem. 1997, 109, 2719-2721; Angew. Chem. Int. Ed. Engl. 1997, 36, 2607-2609;
62. d) A. J. Arduengo III, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall, T. K. Prakasha, J. Am. Chem. Soc. 1997, 119, 12742-12749.
63. G. M. Sheldrick, SHELXL-93, program for crystal structure refinement, Universität Göttingen, 1993.