A dynamically inverting π-bowl complex

Angewandte Chemie - International Edition

Volumn 49, Issue 2, 2010, Pages 403-406

  Amaya, Toru ^a   Wang, Wen Zhen ^a   Sakane, Hiroyuki ^a   Moriuchi, Toshiyuki ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

bowls; Arenes; Inversion; Ruthenium; Sumanene

Indexed keywords

ARENES; CHEMICAL EQUATIONS; DYNAMIC INVERSION; NMR STUDIES; SUMANENE; SUPER BOWL; TEMPERATURE DEPENDENT;

CHEMICAL REACTIONS; METAL COMPLEXES; RUTHENIUM; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

AROMATIC COMPOUNDS;

EID: 73349089963     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200905567     Document Type: Article

References (45)

1. P. J. Fagan, J. C. Calabrese, B. Malone, Science 1991,252,1160-1161.
2. A. L. Balch, M. M. Olmstead, Chem. Rev. 1998, 98, 2123-2165.
3. M. A. Petrukhina, Coord. Chem. Rev. 2007, 251,1690-1698.
4. a) Y-T. Wu, J.S. Siegel, Chem. Rev. 2006, 106, 4843-4867;
5. b) V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106,4868-4884.
6. For previous work within the group on sumanene, see : a) H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878;
7. b) H. Sakurai, T. Daiko, H. Sakane, T. Amaya, T. Hirao, J. Am. Chem. Soc. 2005,127,11580-11581;
8. c) T. Amaya, K. Mori, H.-L. Wu, S. Ishida, J. Nakamura, K. Murata, T. Hirao, Chem. Commun. 2007, 1902-1904;
9. d) T. Amaya, S. Seki, T. Moriuchi, K. Nakamoto, T. Nakata, H. Sakane, A. Saeki, S. Tagawa, T. Hirao, J. Am. Chem. Soc. 2009, 131, 408-409;
10. e) T. Amaya, T. Nakata, T. Hirao, J. Am. Chem. Soc. 2009,131,10810-10811.
11. a) T. J. Seiders, K. K. Baldridge, J. M. O'Connor, J. S. Siegel, J. Am. Chem. Soc. 1997, 119, 4781-4782;
12. b) C. M. Alvarez, R. J. Angelici, A. Sygula, R. Sygula, P. W Rabideau, Organometallics 2003, 22, 624-626;
13. c) M. A. Petrukhina, K. W Andreini, J. Mack, L. T. Scott, Angew. Chem. 2003, 115, 3497-3501;
14. Angew. Chem. Int. Ed. 2003, 42, 3375-3379;
15. d) T.J. Seiders, K. K. Baldridge, J. M. O'Connor, J. S. Siegel, Chem. Commun. 2004, 950-951;
16. e) P. A. Vecchi, C.M. Alvarez, A. Ellern, R.J. Angelici, A. Sygula, R. Sygula, P. W Rabideau, Angew. Chem. 2004, 116, 4597-4600;
17. Angew. Chem. Int. Ed. 2004, 43, 4497-4500;
18. f) M. A. Petrukhina, K. W Andreini, L. Peng, L. T. Scott, Angew. Chem. 2004, 116, 5593-5597;
19. Angew. Chem. Int. Ed. 2004, 43, 5477-5481;
20. g) E. L. Elliott, G.A. Hernández, A. Linden, J. S. Siegel, Org. Biomol. Chem. 2005, 3, 407-413;
21. h)M. A. Petrukhina, K. W Andreini, V.M. Tsefrikas, L. T. Scott, Organometallics 2005, 24, 1394-1397;
22. i)For perspective account: M. A. Petrukhina, L. T. Scott, Dalton Trans. 2005, 2969-2975;
23. j) P. A. Vecchi, C.M. Alvarez, A. Ellern, R.J. Angelici, A. Sygula, R. Sygula, P. W Rabideau, Organometallics 2005, 24, 4543-4552;
24. k) M. A. Petrukhina, Y Sevryugina, A. Y Rogachev, E. A. Jackson, L. T. Scott, Angew. Chem. 2006, 118, 7366-7368;
25. Angew. Chem. Int. Ed. 2006, 45, 7208-7210;
26. M. A. Petrukhina, Y Sevryugina, A. Y Rogachev, E. A. Jackson, L. T. Scott, Organometallics 2006, 25, 5492-5495;
27. m) J. S. Siegel, K. K. Baldridge, A. Linden, R. Dorta, J. Am. Chem. Soc. 2006, 128, 10644-10645;
28. n) B. Zhu, A. Ellern, A. Sygula, R. Sygula, R. J. Angelici, Organometallics 2007, 26, 1721-1728.
29. a) T. Amaya, H. Sakane, T. Hirao, Angew. Chem. 2007, 119, 8528-8531;
30. Angew. Chem. Int. Ed. 2007, 46, 8376-8379;
31. b) For the highlight article, see: M. A. Petrukhina, Angew. Chem. 2008, 120, 1572-1574;
32. Angew. Chem. Int. Ed. 2008, 47, 1550-1552;
33. c) P. Zanello, S. Fedi, F. F. de Biani, G. Giorgi, T. Amaya, H. Sakane, T. Hirao, Dalton Trans. 2009, 9192-9197.
34. H. Sakane, T. Amaya, T. Moriuchi, T. Hirao, Angew. Chem. 2009, 121, 1668-1671;
35. Angew. Chem. Int. Ed. 2009, 48, 1640-1643.
36. a) L. T. Scott, M. M. Hashemi, M. S. Bratcher,J. Am. Chem. Soc. 1992, 114, 1920-1921;
37. b) A. Sygula, A. H. Abdourazak, P. W Rabideau, J. Am. Chem. Soc. 1996, 118, 339-343 ;
38. c) T. J. Seiders, K. K. Baldridge, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 2001, 123, 517-525.
39. T. Amaya, H. Sakane, T. Muneishi, T. Hirao, Chem. Commun. 2008,765-767.
40. 2 has been previously suggested; see Ref. [6j].
41. The dynamic behavior of organometallic compounds has been recognized as fluxionality, and has attracted interest since the 1960s; see F. A. Cotton, Acc. Chem. Res. 1968, 1, 257-265.
42. 1H NMR spectrum (see the Supporting Information).
43. The dissociation-recombination inversion pathway: chemical equation presentation
44. 3] nitromethane; the temperature was varied within the range 253-303 K and 273-313 K, respectively.
45. 3, Z = 4; R1= 0.0989, wR2 = 0.3015. CCDC 736060 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif