An ab initio study on the structure and reactivity of 1,4-disilabenzene

Journal of Organometallic Chemistry

Volumn 611, Issue 1-2, 2000, Pages 280-287

  Kang, Song Yun ^a   Yoshizawa, Kazunari ^a   Yamabe, Tokio ^b   Naka, Akinobu ^c   Ishikawa, Mitsuo ^c  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE FOR FUNDAMENTAL CHEMISTRY   (Japan)

^c KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

1,4 Disilabenzenes; Density functional theory; Dewar type; Diels Alder reaction

Indexed keywords

BETULACEAE;

EID: 0011935203     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00495-2     Document Type: Article

References (61)

1. S. Patai, Z. Rappoport, The Chemistry of Organic Silicon Compounds, Wiley, New York, 1989.
2. Z. Rappoport, Y. Apeloig, The Chemistry of Organic Silicon Compounds, vol. 2, Wiley, New York, 1998.
3. A.G. Brook, F. Abdesaken, B. Gutekunst, G. Gutekunst, R.K. Kallury, J. Chem. Soc. (1981) 191.
4. R. West, M.J. Fink, J. Michl, Science 214 (1981) 1343.
5. G. Raabe, J. Michl, Chem. Rev. 85 (1985) 419.
6. T.J. Barton, D.S. Banasiak, J. Am. Chem. Soc. 99 (1977) 5199.
7. T.J. Barton, D.S. Banasiak, J. Organomet. Chem. 157 (1978) 255.
8. T.J. Barton, G.T. Burns, J. Am. Chem. Soc. 100 (1978) 5246.
9. G. Märkl, P. Hofmeister, Angew. Chem. Int. Ed. Engl. 18 (1979) 789.
10. H. Bock, R.A. Bowling, B. Solouki, T.J. Barton, G.T. Burns, J. Am. Chem. Soc. 102 (1980) 429.
11. C.L. Kreil, O.L. Chapman, G.T. Burns, T.J. Barton, J. Am. Chem. Soc. 102 (1980) 841.
12. B. Solouki, P. Rosmus, H. Bock, G. Maier, Angew. Chem. Int. Ed. Engl. 19 (1980) 51.
13. T.J. Barton, M. Vuper, J. Am. Chem. Soc. 103 (1981) 6788.
14. G. Maier, G. Mihm, H.P. Reisenauer, Chem. Ber. 115 (1982) 801.
15. J.D. Rich, R. West, J. Am. Chem. Soc. 104 (1982) 6884.
16. W. Ando, H. Tanikawa, A. Sekiguchi, Tetra. Lett. 24 (1983) 4245.
17. H. Bock, P. Rosmus, B. Solouki, G. Maier, J. Organomet. Chem. 271 (1984) 145.
18. G. Maier, G. Mihm, R.O.W. Baumgärtner, H.P. Reisenauer, Chem. Ber. 117 (1984) 2337.
19. G. Maier, K. Schöttler, H.P. Reisenauer, Tetra. Lett. 26 (1985) 4079.
20. G. Märkl, W. Schlosser, Angew. Chem. Int. Ed. Engl. 27 (1988) 963.
21. A. Sekiguchi, G.R. Gillette, R. West, Organometallics 7 (1988) 1226.
22. Y.v.d. Winkel, B.L.M.v. Baar, F. Bickelhaupt, W. Kulik, C. Sierakowski, G. Maier, Chem. Ber. 124 (1991) 185.
23. H. Hiratsuka, M. Tanaka, T. Okutsu, M. Oba, K. Nishiyama, J. Chem. Soc. Chem. Commun. (1995) 215.
24. N. Tokitoh, K. Wakita, R. Okazaki, S. Nagase, P.v.R. Schleyer, H. Jiao, J. Am. Chem. Soc. 119 (1997) 6951.
25. T. Müller, Angew. Chem. Int. Ed. 37 (1998) 68.
26. K. Wakita, N. Tokitoh, R. Okazaki, S. Nagase, P.v.R. Schleyer, H. Jiao, J. Am. Chem. Soc. 121 (1999) 11336.
27. K. Wakita, N. Tokitoh, T. Kawashima, R. Okazaki, S. Nagase, Proceedings of 76th National Meeting of the Chemical Society of Japan, Tokyo, March 1999, Abstr., No. 3B510.
28. M.J.S. Dewar, D.H. Lo, C.A. Ramsden, J. Am. Chem. Soc. 97 (1975) 1311.
29. H.B. Schlegel, B. Coleman, M. Jones, Jr., J. Am. Chem. Soc. 100 (1978) 6499.
30. P.H. Blustin, J. Organomet. Chem. 166 (1979) 21.
31. J. Chandrasekhar, P.v.R. Schleyer, R.O.W. Baumgärtner, M.T. Reetz, J. Org. Chem. 48 (1983) 3453.
32. M.S. Gordon, P. Boudjouk, F. Anwari, J. Am. Chem. Soc. 105 (1983) 4972.
33. K.K. Baldridge, M.S. Gordon, J. Organomet. Chem. 271 (1984) 369.
34. J. Chandrasekhar, P.v.R. Schleyer, J. Organomet. Chem. 289 (1985) 51.
35. K.K. Baldridge, M.S. Gordon, J. Am. Chem. Soc. 110 (1988) 4204.
36. H.J. Hofmann, R. Cimiraglia, M. Persico, Chem. Phys. Lett. 146 (1988) 249.
37. H. Bock, Angew. Chem. Int. Ed. Engl. 28 (1989) 1627.
38. Y. Kabe, Proceedings of The Fifth Symposium on the Chemistry of Inter-element Linkage, Kyoto, 2000, p. 85.
39. W. Ando, T. Shiba, T. Hidaka, K. Morihashi, O. Kikuchi, J. Am. Chem. Soc. 119 (1997) 3629.
40. R. Hoffmann, R.B. Woodward, J. Am. Chem. Soc. 87 (1965) 2046.
41. R.B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Verlag, Weinheim, 1970.
42. R.P. Johnson, K.J. Daoust, J. Am. Chem. Soc. 118 (1996) 7381.
43. K. Fukui, J. Phys. Chem. 74 (1970) 4161.
44. K. Fukui, Acc. Chem. Res. 14 (1981) 363.
45. A.D. Becke, Phys. Rev., Sect. A 38 (1988) 3098.
46. A.D. Becke, J. Chem. Phys. 98 (1993) 5648.
47. C. Lee, W. Yang, R.G. Parr, Phys. Rev. Sect. B 37 (1988) 785.
48. E. Goldstein, B. Beno, K.N. Houk, J. Am. Chem. Soc. 118 (1996) 6036.
49. C. Gonzalez, H.B. Schlegel, J. Phys. Chem. 94 (1990) 5523.
50. D. Hegarty, M.A. Robb, Mol. Phys. 38 (1979) 1795.
51. R.H.E. Eade, M.A. Robb, Chem. Phys. Lett. 83 (1981) 362.
52. W.J. Hehre, R. Ditchfield, J.A. Pople, J. Chem. Phys. 56 (1972) 2257.
53. P.C. Hariharan, J.A. Pople, Theor. Chim. Acta 28 (1973) 213.
54. M.S. Gordon, Chem. Phys. Lett. 76 (1980) 163.
55. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN-98, Gaussian, Pittsburgh, PA, 1998.
56. D.R. Lide, CRC Handbook of Chemistry and Physics, 67, CRC Press, New York, 1986-1987.
57. J. Breulet, H.F. Schaefer III, J. Am. Chem. Soc. 106 (1984) 1221.
58. F. Bernardi, A. Bottoni, M.A. Robb, H.B. Schlegel, G. Tonachini, J. Am. Chem. Soc. 107 (1985) 2260.
59. F. Bernardi, P. Celani, M. Olivucci, M.A. Robb, G. Suzzi-Valli, J. Am. Chem. Soc. 117 (1995) 10531.
60. R.D.J. Froese, J.M. Coxon, S.C. West, K. Morokuma, J. Org. Chem. 62 (1997) 6991.
61. K. Yoshizawa, S.Y. Kang, T. Yamabe, A. Naka, M. Ishikawa, Organometallics 18 (1999) 4637.