Dibenzo[b,e]-7,7,8,8-tetraneopentyl- and dibenzo[b,e]-7,7,8,8-tetraisopropyl-7,8-disilabicyclo[2.2.2]octa-2,5-dienes: Interaction with tetracyanoethylene and transition metal chlorides

Journal of Organometallic Chemistry

Volumn 510, Issue 1-2, 1996, Pages 121-133

  Kyushin, Soichiro ^a   Ikarugi, Masanobu ^a   Takatsuna, Kazutoshi ^a   Goto, Midori ^b   Matsumoto, Hideyuki ^a  

^a GUNMA UNIVERSITY   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

Charge transfer; Crystal structure; Cycloreversion; Group 14; Silane; conjugation

Indexed keywords

EID: 0030596354     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(95)05907-7     Document Type: Article

References (52)

1. For reviews: (a) G. Raabe and J. Michl, Chem. Rev., 85 (1985) 419;
2. (b) R. West, Angew. Chem., Int. Ed. Engl., 26 (1987) 1201;
3. (c) G. Raabe and J. Michl, in S. Patai and Z. Rappoport (eds.), The Chemistry of Organic Silicon Compounds, Wiley, Chichester, 1989, Chapter 17.
4. (a) D.N. Roark and G.J.D. Peddle, J. Am. Chem. Soc., 94 (1972) 5837;
5. (b) T.J. Barton and J.A. Kilgour, J. Am. Chem. Soc., 98 (1976) 7231;
6. (c) T.J. Barton and J.A. Kilgour, J. Am. Chem. Soc., 98 (1976) 7746;
7. (d) H. Sakurai, Y. Nakadaira and T. Kobayashi, J. Am. Chem. Soc., 101 (1979) 487;
8. (e) J.D. Rich, T.J. Drahnak, R. West and J. Michl, J. Organomet. Chem., 212 (1981) C1;
9. (f) Y. Nakadaira, T. Otsuka and H. Sakurai, Tetrahedron Lett., 22 (1981) 2417;
10. (g) S. Masamune, S. Murakami and H. Tobita, Organometallics, 2 (1983) 1464;
11. (h) H. Sakurai, Y. Nakadaira and H. Sakaba, Organometallics, 2 (1983) 1484;
12. (i) A. Sekiguchi, I. Maruki, K. Ebata, C. Kabuto and H. Sakurai, J. Chem. Soc., Chem. Commun., (1991) 341.
13. Y. Nakadaira, Y. Gomi, H. Hosoe, S. Kyushin, M. Kako, K. Hatakenaka and M. Ohashi, Bull. Chem. Soc. Jpn., 66 (1993) 344.
14. (a) S. Kyushin, Y. Izumi, S. Tsunakawa and H. Matsumoto, Chem. Lett., (1992) 1393;
15. (b) S. Kyushin, M. Ikarugi, S. Tsunakawa, Y. Izumi, M. Miyake, M. Sato, H. Matsumoto and M. Goto, J. Organomet. Chem., 473 (1994) 19.
16. H. Matsumoto, T. Arai, H. Watanabe and Y. Nagai, J. Chem. Soc., Chem. Commun., (1984) 724.
17. (a) T.G. Traylor, W. Hanstein, H.J. Berwin, N.A. Clinton and R.S. Brown, J. Am. Chem. Soc., 93 (1971) 5715;
18. (b) H. Sakurai, S. Tasaka and M. Kira, J. Am. Chem. Soc., 94 (1972) 9285.
19. It has been reported that charge-transfer bands of silyl-substituted benzene-TCNE complexes are well simulated by skewed Gaussian lines [25]. However, the charge-transfer bands of 1 and 2 with TCNE could not be simulated by two skewed Gaussian lines because the width of the higher-energy band is significantly larger than that of the lower-energy band. It seems that the charge-transfer bands consist of more than two components.
20. For a review: V.F. Traven and S.Y. Shapakin, Adv. Organomet. Chem., 34 (1992) 149.
21. (a) H. Bock and H. Alt, Angew. Chem., Int. Ed. Engl., 6 (1967) 942;
22. (b) H. Bock, H. Seidl and M. Fochler, Chem. Ber., 101 (1968) 2815;
23. (c) W. Hanstein, H.J. Berwin and T.G. Traylor, J. Am. Chem. Soc., 92 (1970) 829;
24. (d) H. Bock and H. Alt, J. Am. Chem. Soc., 92 (1970) 1569;
25. (e) C.G. Pitt, J. Organomet. Chem., 23 (1970) C35;
26. (f) H. Sakurai, M. Kira and M. Ochiai, Chem. Lett., (1972) 87;
27. (g) V.F. Traven and R. West, J. Am. Chem. Soc., 95 (1973) 6824;
28. (h) H. Sakurai, M. Kira and T. Uchida, J. Am. Chem. Soc., 95 (1973) 6826;
29. (i) H. Sakurai and M. Kira, J. Am. Chem. Soc., 96 (1974) 791;
30. (j) H. Sakurai, K. Sakamoto and M. Kira, Chem. Lett., (1984) 1213;
31. (k) H. Sakurai, M. Ichinose, M. Kira and T.G. Traylor, Chem. Lett., (1984) 1383;
32. (l) M. Kira, K. Takeuchi, C. Kabuto and H. Sakurai, Chem. Lett., (1988) 353.
33. S. Kyushin, Y. Ohkura, Y. Nakadaira, M. Ohashi, M. Yasui, M. Matsui and F. Iwasaki, Chem. Lett., (1991) 883.
34. A referee pointed out the possibility of the participation of electron transfer in the cycloreversion. We think that electron transfer is probable as reported in the cycloreversion of 2,3-disilabicyclo[2.2.2]octa-5,7-diene derivatives via photo-induced electron transfer [3].
35. (a) H. Sakurai, Y. Kamiyama and Y. Nakadaira, J. Am. Chem. Soc., 97 (1975) 931;
36. (b) H. Sakurai, Y. Kamiyama and Y. Nakadaira, Chem. Lett., (1975) 887;
37. (c) C.W. Carlson and R. West, Organometallics, 2 (1983) 1801;
38. (d) A. Schäfer, M. Weidenbruch and S. Pohl, J. Organomet. Chem., 282 (1985) 305;
39. (e) M. Ishikawa, S. Okazaki, A. Naka and H. Sakamoto, Organometallics, 11 (1992) 4135.
40. D.R. Hepburn and H.R. Hudson, J. Chem. Soc., Perkin Trans. 1, (1976) 754.
41. J.R. Doyle, P.E. Slade and H.B. Jonassen, Inorg. Synth., 6 (1960) 216.
42. J.M. Jenkins and B.L. Shaw, J. Chem. Soc., Sect. A, (1966) 770.
43. K.A. Hofmann and G. Bugge, Ber., 40 (1907) 1772.
44. G.W. Parshall, Inorg. Synth., 12 (1970) 27.
45. J.A. Osborn and G. Wilkinson, Inorg. Synth., 10 (1967) 67.
46. R.R. Schrock and J.D. Fellmann, J. Am. Chem. Soc., 100 (1978) 3359.
47. S.C. Watson and J.F. Eastham, J. Organomet. Chem., 9 (1967) 165.
48. P. Main, S.J. Fiske, S.E. Hull, L. Lessinger, G. Germain, J.-P. Declercq and M.M. Woolfson, MULTAN80, A System of Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data, Universities of York, UK and Louvain, Belgium, 1980.
49. P. Main, S.E. Hull, L. Lessinger, G. Germain, J.-P. Declercq and M.M. Woolfson, MULTAN78, A System of Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data, Universities of York, UK and Louvain, Belgium, 1978.
50. T. Sakurai and K. Kobayashi, Rikagaku Kenkyusho Hokoku, 55 (1979) 69.
51. D.T. Cromer and J.T. Waber, International Tables for X-ray Crystallography, Vol. IV, Kynoch, Birmingham, UK, 1974, Table 2.3.1.
52. H. Sakurai and M. Kira, J. Am. Chem. Soc., 97 (1975) 4879.