An η6-dienyne transition-metal complex

Journal of the American Chemical Society

Volumn 127, Issue 26, 2005, Pages 9346-9347

  O'Connor, Joseph M ^a   Friese, Seth J ^a   Rodgers, Betsy L ^a   Rheingold, Arnold L ^a   Zakharov, Lev ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; TRANSITION ELEMENT;

AROMATIZATION; ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID STATE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 21644475747     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042272y     Document Type: Article

References (22)

1. For leading references: (a) Donaldson, W. A. Curr. Org. Chem. 2000, 4, 837-868.
2. (b) Rigby, J. H.; Mundruppady, L. S.; Hudson, A. R.; Heap, C. H.; Heeg, M. J. J. Org. Chem. 2004, 69, 6751.
3. Kukushkin, Y. N.; Pakhomova, I. V.; Arbatov, A. N. Zh. Obshch. Khim. 1984, 54, 1595-1598.
4. (a) O'Connor, J. M.; Preise, S. J.; Tichenor, M. J. Am. Chem. Soc. 2002, 124, 3506-3507.
5. (b) O'Connor, J. M.; Lee, L. I.; Gantzel, P.; Rheingold, A. L.; Lam, K. C. J. Am. Chem. Soc. 2000, 122, 12057-12058.
6. For leading references: (a) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495.
7. (b) Pearson, A. L.; Lee, K. J. Org. Chem. 1994, 59, 2304-2313.
8. Dembek, A. A.; Pagan, P. J. Organometallics 1996, 15, 1319-1322.
9. Kündig, E. P.; Monnier, F. R. Adv. Synth. Catal. 2004, 346, 901-904.
10. (a) For a ruthenium-catalyzed aromatization of dienynes that involves vinylidene intermediates and leads to 1,2-halide shifts, see: Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763.
11. (b) The position of the chloride in 7-Cp was confirmed by an X-ray crystallographic analysis.
12. + reversibly coordinates to the dienyne. (Diagram presented)
13. (a) Trakarnpruk, W.; Arif, A. M.; Ernst, R. D. Organometallics 1992. 11, 1686-1692.
14. (b) Bosch, H. W.; Hund, H.-U.; Nietlispach, D.; Salzer, A. Organometallics 1992, 11, 2087-2098.
15. 2-C≡CR angle range 151-155°): Casey, C. P.; Selmeczy, A. D.; Nash, J. R.; Yi, C. S.; Powell, D. R.; Hayashi, R. K. J. Am. Chem. Soc. 1996, 118, 6698-6706.
16. H(1A)/H(1B) were refined with isotropic thermal parameters.
17. Van der Boom, M. E.; Iron, M. A.; Atasoylu, O.; Shimon, L. J. W.; Rozenberg, H.; Ben-David, Y.; Konstantinovski, L.; Martin, L. M. L.; Milstein, D. Inorg. Chim. Acta 2004, 357, 1854-1864.
18. If the alkyne in 10 is a two-electron donor, then the Ru-H(IB) nonbonded interaction must be repulsive rather than attractive.
19. 13c,d (a) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319-11320.
20. (b) See ref 6a.
21. (c) Herndon, J. W.; Zhang, Y.; Wang, K. J. Organomet. Chem. 2001, 634, 1-4.
22. Martin-Matute, B.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5766.