Preparation and properties of phosphaethynes bearing bulky aryl groups with electron-donating substituents at the para position

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 5065-5070

  Toyota, Kozo ^a   Kawasaki, Subaru ^a   Yoshifuji, Masaaki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BATHOCHROMIC SHIFTS; ELECTRON DONATING GROUPS;

HYDROCARBONS;

2 [2,6 DI TERT BUTYL 4 (DIMETHYLAMINO)PHENYL] 1 PHOSPHAETHYNE; 2,6 DI TERT BUTYL 4 (DIMETHYLAMINO)PHENYL 1 PHOSPHAETHYNE; 2,6 DI TERT BUTYL 4 METHOXYPHENYL 1 PHOSPHAETHYNE; 2,6 DI TERT BUTYLPHENYL 1 PHOSPHAETHYNE; ACETYLENE DERIVATIVE; PHOSPHAETHYNE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 3543039435     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049571q     Document Type: Article

References (74)

1. For recent reviews, (a) Power, P. P. Chem. Rev. 1999, 99, 3463.
2. (b) Weidenbruch, M. Eur. J. Inorg. Chem. 1999, 373.
3. (c) Grützmacher, H.; Fässler, T. F. Chem. Eur. J. 2000, 2317.
4. (d) Jutzi, P. Angew. Chem., Int. Ed. 2000, 39, 3797.
5. (e) Escudié, J.; Ranaivonjatovo, H.; Rigon, L. Chem. Rev. 2000, 100, 3639.
6. (f) Weber, L. Angew. Chem., Int. Ed. 2002, 41, 563.
7. (g) Weidenbruch, M. Angew. Chem., Int. Ed. 2003, 42, 2222.
8. (h) Power, P. P. Chem. Commun. 2003, 2091.
9. (a) Dimroth, K.; Hoffmann, P. Angew. Chem., Int. Ed. Engl. 1964, 3, 384.
10. (b) Märkl, G. Angew. Chem., Int. Ed. Engl. 1966, 5, 846.
11. (c) Becker, G. Z. Anorg. Allg. Chem. 1978, 423, 242.
12. For example: (a) Arya, P.; Boyer, J.; Carré, F.; Corriu, R. J. P.; Lanneau, G.; Lapasset, J.; Perrot, M.; Priou, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1016.
13. (b) Schmidt, H.; Keitemeyer, S.; Neumann, B.; Stammler, H.-G.; Schoeller, W. W.; Jutzi, P. Organometallics 1998, 17, 2149.
14. (c) Jutzi, P.; Keitemeyer, S.; Neumann, B.; Stammler, H.-G. Organometallics 1999, 18, 4778.
15. (d) Jutzi, P.; Keitemeyer, S.; Neumann, B.; Stammler, A.; Stammler, H.-G. Organometallics 2001, 20, 42.
16. (e) Verkade, J. G. Acc. Chem. Res. 1993, 26, 483.
17. (f) Yoshifuji, M.; Hirano, M.; Toyota, K. Tetrahedron Lett. 1993, 34, 1043.
18. (g) Yoshifuji, M.; An, D.-L.; Toyota, K.; Yasunami, M. Chem. Lett. 1993, 2069.
19. (h) Yoshifuji, M.; Sangu, S.; Kamijo, K.; Toyota, K. Chem. Ber. 1996, 129, 1049.
20. For example: (a) Klebach, Th. C.; Lourens, R.; Bickelhaupt, F. J. Am. Chem. Soc. 1978, 100, 4886.
21. (b) Yoshifuji, M.; Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1981, 103, 4587.
22. (c) Yoshifuji, M.; Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1982, 104, 6167.
23. (d) West, R.; Fink, M. J.; Michl, J. Science 1981, 214, 1343.
24. (e) Tokitoh, N.; Arai, Y.; Okazaki, R.; Nagase, S. Science 1997, 277, 78.
25. (f) Stender, M.; Phillips, A. D.; Wright, R. J.; Power, P. P. Angew. Chem., Int. Ed. 2002, 41, 1785.
26. (a) Regitz, M.; Scherer, O. J. Multiple Bonds and Low Coordination in Phosphorus Chemistry; Georg Thieme Verlag: Stuttgart, Germany, 1990, and references therein.
27. (b) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; John Wiley: Chichester, UK, 1998.
28. (c) Yoshifuji, M. J. Organomet. Chem. 2000, 611, 210.
29. For example: (a) Issleib, K.; Schmidt, H.; Wirkner, C. Z. Anorg. Allg. Chem. 1982, 488, 75.
30. (b) Yoshifuji, M.; Toyota, K.; Inamoto, N. Tetrahedron Lett. 1985, 26, 1727.
31. For example: (a) Gier, T. E. J. Am. Chem. Soc. 1961, 83, 1769.
32. (b) Kroto, H. W.; Nixon, J. F.; Simmons, N. P. C.; Westwood, N. P. C. J. Am. Chem. Soc. 1978, 100, 446.
33. (c) Hopkinson, M. J.; Kroto, H. W.; Nixon, J. F.; Simmons, N. P. C. Chem. Phys. Lett. 1976, 42, 460.
34. (d) Becker, G.; Gresser, G.; Uhl, W. Z. Naturforsch. B 1981, 36, 16.
35. (e) Allspach, T.; Regitz, M.; Becker, G.; Becker, W. Synthesis 1986, 31.
36. (f) Appel, R.; Westerhaus, A. Tetrahedron Lett. 1981, 22, 2159.
37. (g) Ohno, K.; Kroto, H. W.; Nixon, J. F. J. Mol. Spectrosc. 1981, 90, 507.
38. (h) Kroto, H. W.; Nixon, J. F.; Ohno, K. J. Mol. Spectrosc. 1981, 90, 512.
39. (i) Cooper, T. A.; Kroto, H. W.; Nixon, J. F.; Ohashi, O. J. Chem. Soc., Chem. Commun. 1980, 333.
40. (j) Markovskii, L. N.; Koidan, G. N.; Marchenko, A. P.; Romanenko, V. D.; Povolotskii, M. I.; Pinchuk, A. M. Zh. Obshch. Khim. 1989, 59, 2133.
41. (k) Grobe, J.; Le Van, D.; Lüth, B.; Hegemann, M. Chem. Ber. 1990, 123, 2317.
42. (l) Grobe, J.; Le Van, D.; Pohlmeyer, T.; Immel, F.; Pucknat, H.; Krebs, B.; Kuchinke, J.; Läge, M. Tetrahedron 2000, 56, 27 and references therein.
43. (a) Appel, R.; Maier, G.; Reisenauer, H. P.; Westerhaus, A. Angew. Chem., Int Ed Engl. 1981, 20, 197.
44. (b) Mack, A.; Pierron, E.; Allspach, T.; Bergsträsser, U.; Regitz, M. Synthesis 1998, 1305.
45. (c) Märkl, G.; Sejpka, H. Tetrahedron Lett. 1986, 27, 171.
46. (d) Yoshifuji, M.; Kawanami, H.; Kawai, Y.; Toyota, K.; Yasunami, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1992, 1053.
47. (e) Fleischer, U.; Kutzelnigg, W. Phosphorus, Sulfur, Silicon 1993, 77, 105.
48. For example: (a) Appel, R.; Hünerbein, J.; Siabalis, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 779.
49. (b) Ito, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 1995, 747.
50. (c) Appel, R.; Winkhaus, V.; Knoch, F. Chem. Ber. 1987, 120, 243.
51. (d) Toyota, K.; Tashiro, K.; Yoshifuji, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1163.
52. (a) Yoshifuji, M.; Toyota, K.; Shibayama, K.; Inamoto, N. Tetrahedron Lett. 1984, 25, 1809.
53. (b) Yoshifuji, M.; Toyota, K.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1984, 689.
54. (c) Karsch, H. H.; Köhler, F. H.; Reisacher, H.-U. Tetrahedron Lett. 1984, 25, 3687.
55. (d) Appel, R.; Fölling, P.; Josten, B.; Siray, M.; Winkhaus, V.; Knoch, F. Angew. Chem., Int. Ed. Engl. 1984, 23, 619.
56. (e) Märkl, G.; Sejpka, H.; Dietl, S.; Nuber, B.; Ziegler, M. L. Angew. Chem., Int. Ed. Engl. 1988, 25, 1003.
57. (f) Märkl, G.; Kreitmeier, P. Angew. Chem., Int. Ed. Engl. 1988, 27, 1360.
58. (a) Toyota, K.; Kawasaki, S.; Nakamura, A.; Yoshifuji, M. Chem. Lett. 2003, 32, 430.
59. See also: (b) Toyota, K.; Nakamura, A.; Yoshifuji, M. Chem. Commun. 2002, 3012.
60. (c) Toyota, K.; Matsushita, Y.; Shinohara, N.; Yoshifuji, M. Heteroat. Chem. 2001, 12, 418.
61. (a) Rundel, W. Chem. Ber. 1968, 101, 2956.
62. See also: (b) Yoshifuji, M.; Niitsu, T.; Shiomi, D.; Inamoto, N. Tetrahedron Lett. 1989, 30, 5433.
63. Fox, G. J.; Hepworth, J. D.; Paskins, K. N. Org. Synth. 1976, 55, 20.
64. Courtin, A.; von Tobel, H.-R. Helv. Chim. Acta 1977, 60, 1994.
65. Blanksma, J. J. Recl. Trav. Chim. Pays-Bas 1906, 25, 165.
66. Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
67. Goede, S. J.; Bickelhaupt, F. Chem. Ber. 1991, 124, 2677.
68. (a) Sugiyama, H.; Ito, S.; Yoshifuji, M. Angew. Chem., Int. Ed. 2003, 42, 3802.
69. (b) Appel, R.; Immenkeppel, M. Z. Anorg. Allg. Chem. 1987, 553, 7.
70. (c) Yoshifuji, M.; Niitsu, T.; Inamoto, N. Chem. Lett. 1988, 1733.
71. For example: Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90, 4328.
72. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre (No. CCDC-227150).
73. Johnson, C. K. Oak Ridge National Laboratory Report, ORNL-TM-5138, Oak Ridge, TN, 1976.
74. Arif, A. M.; Barren, A. R.; Cowley, A. H.; Hall, S. W. J. Chem. Soc., Chem. Commun. 1988, 171.