Characterization of the e isomer of tetrasubstituted [5]cumulene and trapping of the Z Isomer as a zirconocene complex

Organometallics

Volumn 30, Issue 13, 2011, Pages 3544-3548

  Suzuki, Noriyuki ^a,b   Ohara, Nozomu ^a   Nishimura, Kosuke ^a   Sakaguchi, Yoshio ^b   Nanbu, Shinkoh ^a   Fukui, Sohei ^a   Nagao, Hirotaka ^a   Masuyama, Yoshiro ^a  

^a SOPHIA UNIVERSITY   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CUMULENES; DFT CALCULATION; E-ISOMERS; ELECTROCHEMICAL STUDIES; TRANSITION-METAL COMPLEX; ZIRCONOCENE COMPLEXES;

METAL COMPLEXES; TRANSITION METALS; ZIRCONIUM COMPOUNDS;

ISOMERS;

EID: 79959998217     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2002427     Document Type: Article

References (36)

1. Ogasawara, M. In Cumulenes and Allenes; Krause, N., Ed.; Thieme: Stuttgart, Germany, 2007; Science of Synthesis Vol. 44, pp 9-70.
2. Hino, S.; Okada, Y.; Iwasaki, K.; Kijima, M.; Shirakawa, H. Chem. Phys. Lett. 2003, 372, 59-65
3. Kuhn, R.; Schulz, B.; Jochims, J. C. Angew. Chem., Int. Ed. 1966, 5, 420-420
4. Dewar, M. J. S.; Haselbach, E. J. Am. Chem. Soc. 1970, 92, 590-598
5. Bertsch, K.; Karich, G.; Jochims, J. C. Chem. Ber. 1977, 110, 3304-3313
6. Skibar, W.; Kopacka, H.; Wurst, K.; Salzmann, C.; Ongania, K.-H.; de Biani, F. F.; Zanello, P.; Bildstein, B. Organometallics 2004, 23, 1024-1041
7. For example, see: Kuwatani, Y.; Yamamoto, G.; Oda, M.; Iyoda, M. Bull. Chem. Soc. Jpn. 2005, 78, 2188-2208
8. Suzuki, N.; Nishiura, M.; Wakatsuki, Y. Science 2002, 295, 660-663
9. Suzuki, N.; Aihara, N.; Takahara, H.; Watanabe, T.; Iwasaki, M.; Saburi, M.; Hashizume, D.; Chihara, T. J. Am. Chem. Soc. 2004, 126, 60-61
10. Suzuki, N.; Hashizume, D.; Koshino, H.; Chihara, T. Angew. Chem., Int. Ed. 2008, 47, 5198-5202
11. Suzuki, N.; Hashizume, D.; Yoshida, H.; Tezuka, M.; Ida, K.; Nagashima, S.; Chihara, T. J. Am. Chem. Soc. 2009, 131, 2050-2051
12. Suzuki, N. Bull. Jpn. Soc. Coord. Chem. 2009, 53, 43-57
13. Suzuki, N.; Hashizume, D. Coord. Chem. Rev. 2010, 254, 1307-1326 See also: Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U.; Parameswaran, P.; Jemmis, E. D. Chem. Commun. 2004, 2074-2075
14. Bach, M. A.; Beweries, T.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A.; Rosenthal, U. Organometallics 2007, 26, 4592-4597
15. Yamazaki, S. Inorg. Chim. Acta 2011, 366, 1-18
16. There have been some [5]cumulene complexes: King, R. B.; Harmon, C. A. J. Organomet. Chem. 1975, 88, 93-100
17. Werner, H.; Wiedemann, R.; Mahr, N.; Steinert, P.; Wolf, J. Chem. Eur. J. 1996, 2, 561-569
18. Song, L.; Arif, A. M.; Stang, P. J. J. Organomet. Chem. 1990, 395, 219-226
19. Iyoda, M.; Kuwatani, Y.; Oda, M. J. Chem. Soc., Chem. Commun. 1992, 399-400
20. Iyoda, M.; Kuwatani, Y.; Oda, M.; Tatsumi, K.; Nakamura, A. Angew. Chem., Int. Ed. Engl. 1991, 30, 1670-1672
21. Woolfson, M. M. Acta Crystallogr. 1953, 6, 838
22. Irngartinger, H.; Jäger, H.-U. Angew. Chem., Int. Ed. Engl. 1976, 15, 562-563
23. Suzuki, N.; Hashizume, D.; Chihara, T. Acta Crystallogr., Sect. E 2007, E63, o3436
24. For electrochemical studies on [5]cumulenes, see: Bildstein, B.; Schweiger, M.; Angleitner, H.; Kopacka, H.; Wurst, K.; Ongania, K.-H.; Fontani, M.; Zanello, P. Organometallics 1999, 18, 4286-4295
25. Kool, L. B.; Rausch, M. D.; Alt, H. G.; Herberhold, M.; Honold, B.; Thewalt, U. J. Organomet. Chem. 1987, 320, 37-45
26. Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1990, 23, 4485-4486
27. SIR92: Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435
28. DIRDIF99: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-99 Program System; Technical Report of the Crystallography Laboratory, University of Nijmegen, Nijmegen, The Netherlands, 1999.
29. CrystalStructure 3.8: Crystal Structure Analysis Package; Rigaku and Rigaku Americas, 9009 New Trails Dr., The Woodlands TX 77381, 2000, - 2007.
30. Sheldrick, G. M. SHELX97; University of Göttingen, Göttingen, Germany, 1997.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
32. Lee, C. X.; Yang, W. X.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
33. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265-3269
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C; Farkas, O.; Tomasi, J.; Barone, V; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C; Adamo, C; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, X; Al-Laham, M. A.; Peng, C. Y; Nanayakkara, A.; Challacombe, M.; P. Gill; M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, Revision B.5; Gaussian, Inc., Pittsburgh, PA, 2003.
35. Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358-1371
36. SIR2004: Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Cryst. 2005, 38, 381-388