A planar rhombic charge-separated tetrasilacyclobutadiene

Science

Volumn 331, Issue 6022, 2011, Pages 1306-1309

  Suzuki, Katsunori ^a   Matsuo, Tsukasa ^a   Hashizume, Daisuke ^a   Fueno, Hiroyuki ^b   Tanaka, Kazuyoshi ^b   Tamao, Kohei ^a  

^a RIKEN   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYCLOBUTANE DERIVATIVE; LITHIUM; SILICON; TETRASILACYCLOBUTADIENE; UNCLASSIFIED DRUG;

CHEMICAL COMPOSITION; CRYSTALLOGRAPHY; GEOMETRY; HYDROCARBON; LITHIUM; NUCLEAR MAGNETIC RESONANCE; SILICON;

ARTICLE; CHEMICAL STRUCTURE; GEOMETRY; MOLECULE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY CRYSTALLOGRAPHY;

EID: 79952514523     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1199906     Document Type: Article

References (43)

1. L. Watts, J. D. Fitzpatrick, R. Pettit, J. Am. Chem. Soc. 87, 3253 (1965).
2. T. Bally, S. Masamune, Tetrahedron 36, 343 (1980).
3. G. Maier, Angew. Chem. Int. Ed. Engl. 27, 309 (1988).
4. T. Bally, Angew. Chem. Int. Ed. 45, 6616 (2006).
5. C. Y. Lin, A. Krantz, J. Chem. Soc. Chem. Commun. 1972, 1111 (1972).
6. D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. Int. Ed. Engl. 30, 1024 (1991).
7. A. A. Deniz, K. S. Peters, G. J. Snyder, Science 286, 1119 (1999).
8. A. Fattahi, L. Lis, Z. Tian, S. R. Kass, Angew. Chem. Int. Ed. 45, 4984 (2006).
9. A. M. Orendt et al., J. Am. Chem. Soc. 110, 2648 (1988).
10. B. R. Arnold, J. G. Radziszewski, A. Campion, S. S. Perry, J. Michl, J. Am. Chem. Soc. 113, 692 (1991).
11. A. Balková, R. J. Bartlett, J. Chem. Phys. 101, 8972 (1994).
12. Push-pull perturbed CBDs provide the localized MOs (38).
13. H. Kimling, A. Krebs, Angew. Chem. Int. Ed. Engl. 11, 932 (1972).
14. H. Irngartinger, H. Rodewald, Angew. Chem. Int. Ed. Engl. 13, 740 (1974).
15. L. T. J. Delbaere, M. N. G. James, N. Nakamura, S. Masamune, J. Am. Chem. Soc. 97, 1973 (1975).
16. G. Maier, S. Pfriem, U. Schäfer, R. Matusch, Angew. Chem. Int. Ed. Engl. 17, 520 (1978).
17. E. J. Petersson et al., J. Am. Chem. Soc. 119, 11122 (1997).
18. J. I. Wu, F. A. Evangelista, P. R. Schleyer, Org. Lett. 12, 768 (2010).
19. Y.-M. Legrand, A. van der Lee, M. Barboiu, Science 329, 299 (2010).
20. K. Wakita, N. Tokitoh, R. Okazaki, S. Nagase, Angew. Chem. Int. Ed. 39, 634 (2000).
21. S. Ishida, T. Iwamoto, C. Kabuto, M. Kira, Nature 421, 725 (2003).
22. M. Weidenbruch, S. Willms, W. Saak, G. Henkel, Angew. Chem. Int. Ed. Engl. 36, 2503 (1997).
23. A. Sekiguchi, R. Kinjo, M. Ichinohe, Science 305, 1755 (2004).
24. Y. Wang et al., Science 321, 1069 (2008).
25. A. G. Brook, F. Abdesaken, B. Gutekunst, G. Gutekunst, R. K. Kallury, J. Chem. Soc. Chem. Commun. 1981, 191 (1981).
26. R. West, M. J. Fink, J. Michl, Science 214, 1343 (1981).
27. K. Abersfelder, A. J. P. White, H. S. Rzepa, D. Scheschkewitz, Science 327, 564 (2010).
28. B. F. Yates, D. A. Clabo Jr., H. F. Schaefer III, Chem. Phys. Lett. 143, 421 (1988).
29. 2h structure was also found in B3LYP/6-31G(d,p) level calculations (36).
30. N. Wiberg, C. M. M. Finger, K. Polborn, Angew. Chem. Int. Ed. Engl. 32, 1054 (1993).
31. M. Ichinohe, M. Toyoshima, R. Kinjo, A. Sekiguchi, J. Am. Chem. Soc. 125, 13328 (2003).
32. K. Takanashi, V. Ya. Lee, T. Matsuno, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 127, 5768 (2005).
33. V. Ya. Lee, K. Takanashi, T. Matsuno, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 126, 4758 (2004).
34. A. Fukazawa, Y. Li, S. Yamaguchi, H. Tsuji, K. Tamao, J. Am. Chem. Soc. 129, 14164 (2007).
35. B. Li et al., J. Am. Chem. Soc. 131, 13222 (2009).
36. Materials and methods are available as supporting material on Science Online.
37. + (where Mes is 2,4,6-trimethylphenyl) in the solid state (42).
38. V. Bonačić-Koutecký, J. Koutecký, J. Michl, Angew. Chem. Int. Ed. Engl. 26, 170 (1987).
39. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. R. Schleyer, Chem. Rev. 105, 3842 (2005).
40. W. Kutzelnigg, Angew. Chem. Int. Ed. Engl. 23, 272 (1984).
41. R. C. Fischer, P. P. Power, Chem. Rev. 110, 3877 (2010).
42. K.-C. Kim et al., Science 297, 825 (2002).
43. Supported by a Grant-in-Aid for Specially Promoted Research (19002008) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. Numerical calculations were partly performed at the Supercomputer Laboratory, Institute for Chemical Research, Kyoto University. We thank Y. Hongo and T. Nakamura (RIKEN) for their kind help with the mass spectrometry and solid-state NMR spectroscopy. We also thank J. Michl, R. Noyori, A. Sekiguchi, and R. West for their valuable discussions. Metric data for the solid-state structure of 1 are available from the Cambridge Crystallographic Data Centre under reference number CCDC-786049.