Isolable p - And m -[(tBu2MeSi)2Si] 2C6H4: Disilaquinodimethane vs triplet bis(silyl radical)

Journal of the American Chemical Society

Volumn 133, Issue 15, 2011, Pages 5773-5775

  Nozawa, Takeshi ^a   Nagata, Michiyo ^a   Ichinohe, Masaaki ^a   Sekiguchi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE BONDS; EPR MEASUREMENTS; REDUCTIVE DEHALOGENATION; SILYL RADICAL; SOLID STATE NMR;

BENZENE; DEHALOGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

X RAY CRYSTALLOGRAPHY;

ALKANE DERIVATIVE; BENZENE DERIVATIVE; CARBON; FREE RADICAL; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; DEHALOGENATION; ISOLATION PROCEDURE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 79954467839     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2014746     Document Type: Article

References (40)

1. Hicks, R. G. Stable Radicals. Fundamentals and Applied Aspects of Odd-Electron Compounds; Wiley: Chichester, 2010.
2. Fujita, I.; Teki, Y.; Takui, T.; Kinoshita, T.; Itoh, K.; Miko, F.; Sawaki, Y.; Iwamura, H.; Izuoka, A.; Sugawara, T. J. Am. Chem. Soc. 1990, 112, 4074
3. Rajca, S.; Rajca, A. J. Am. Chem. Soc. 1995, 117, 9172
4. Lahti, P. M. Magnetic Properties of Organic Materials; Marcel Dekker: New York, 1999.
5. Thiele, J.; Balhorn, H. Chem. Ber. 1904, 37, 1463
6. Montgomery, L. K.; Huffman, J. C.; Jurczak, E. A.; Grendze, M. P. J. Am. Chem. Soc. 1986, 108, 6004
7. Schlenk, W.; Brauns, M. Chem. Ber. 1915, 48, 661
8. Gajewski, J. J.; Chang, M.-J.; Stang, P.-J.; Fisk, T. E. J. Am. Chem. Soc. 1980, 102, 2096
9. Wright, B. B.; Platz, M. S. J. Am. Chem. Soc. 1983, 105, 628
10. Rajca, A.; Utamapanya, S. J. Am. Chem. Soc. 1993, 115, 2396
11. Neuhaus, P.; Sander, W. Angew. Chem., Int. Ed. 2010, 49, 7277
12. Reviews: Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229
13. Iley, J. In The Chemistry of Organic Germanium, Tin and Lead Compounds; Patai, S., Ed.; Wiley: Chichester, 1995; Chapter 5.
14. Chatgilialoglu, C.; Ferreri, C.; Gimisis, T. In The Chemistry of Organic Silicon Compounds, Vol. 2, Part 2; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 1998; Chapter 25.
15. Chatgilialoglu, C.; Schiesser, C. H. In The Chemistry of Organic Silicon Compounds, Vol. 3; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 2001; Chapter 4.
16. Carland, M. W.; Schiesser, C. H. In The Chemistry of Organic Germanium, Tin and Lead Compounds, Vol. 2, Part 2; Rappoport, Z., Ed.; Wiley: Chichester, 2002; Chapter 19.
17. Chatgilialoglu, C. Chem.-Eur. J. 2008, 14, 2310
18. Chatgilialoglu, C.; Timokhin, V. I. Adv. Organomet. Chem. 2008, 57, 117
19. Davidson, P. J.; Hudson, A.; Lappert, M. F.; Lednor, P. W. J. Chem. Soc., Chem. Commun. 1973, 829
20. Cotton, J. D.; Cundy, C. S.; Harris, D. H.; Hudson, A.; Lappert, M. F.; Lednor, P. W. J. Chem. Soc., Chem. Commun. 1974, 651
21. Hudson, A.; Lappert, M. F.; Lednor, P. W. J. Chem. Soc., Dalton Trans. 1976, 2369
22. Olmstead, M. M.; Pu, L.; Simons, R. S.; Power, P. P. Chem. Commun. 1997, 1595
23. Sekiguchi, A.; Matsuno, T.; Ichinohe, M. J. Am. Chem. Soc. 2001, 123, 12436
24. Sekiguchi, A.; Fukawa, T.; Nakamoto, M.; Lee, V. Ya.; Ichinohe, M. J. Am. Chem. Soc. 2002, 124, 9865
25. Ishida, Y.; Sekiguchi, A.; Kobayashi, K.; Nagase, S. Organometallics 2004, 23, 4981
26. Sekiguchi, A.; Fukawa, T.; Lee, V. Ya.; Nakamoto, M. J. Am. Chem. Soc. 2003, 125, 9250
27. Förster, C.; Klinkhammer, K. W.; Tumanskii, B.; Krüger, H.-J.; Kelm, H. Angew. Chem., Int. Ed. 2007, 46, 1156
28. Becker, M.; Förster, C.; Franzen, C.; Harthrath, J.; Kirsten, E.; Knuth, J.; Klinkhammer, K. W.; Sharma, A.; Hinderberger, D. Inorg. Chem. 2008, 47, 9965
29. Reviews on the persistent and stable heavy group 14 element-centered free radicals: Power, P. P. Chem. Rev. 2003, 103, 789
30. Lee, V. Ya.; Sekiguchi, A. Eur. J. Inorg. Chem. 2005, 1209
31. Lee, V. Ya.; Sekiguchi, A. Acc. Chem. Res. 2007, 40, 410
32. Lee, V. Ya.; Sekiguchi, A. In Reviews of Reactive Intermediates Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley: Hoboken, 2007; Chapter 2.
33. Lee, V. Ya.; Sekiguchi, A. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb: From Phantom Species to Stable Compounds; Wiley: Chichester, 2010; Chapter 2.
34. Reduction of the corresponding 1,3-bis(bromosilyl)benzene derivative with potassium graphite in THF failed to produce the desired 4.
35. For the synthesis as well as spectral and crystal data of new compounds 1 - 7, see the Supporting Information.
36. Kaftory, M.; Kapon, M.; Botoshansky, M. In The chemistry of Organic Silicon Compounds, Vol. 2, Part 1; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 1998; Chapter 5.
37. See ref 12e, Chapter 5.
38. 4 were performed at the DFT UB3LYP/6-31 g(d) level using the GAUSSIAN03 program package.
39. For temperature-dependent EPR measurements of 4, see the Supporting Information.
40. Berson, J. A. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Eds.; Wiley: Hoboken, 2004; Chapter 5.