Double Group Transfer Reactions of an Unsaturated Tantalum Methylidene Complex with Pyridine N-Oxides

Organometallics

Volumn 18, Issue 22, 1999, Pages 4465-4467

  Mullins, Sarah M ^a   Bergman, Robert G ^a   Arnold, John ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 17544402646     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9906870     Document Type: Article

References (24)

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2. Schrock, R. R. Acc. Chem. Res. 1979, 12, 98.
3. Schrock, R. R. Science 1983, 219, 13.
4. Gunnoe, T. B.; White, P. S.; Templeton, J. L.; Casarrubios, L. J. Am. Chem. Soc. 1997, 119, 3171.
5. Doyle, M. Chem. Rev. 1986, 86, 919.
6. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
7. Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
8. The synthesis of 1 was originally reported in: Dawson, D. Y., Arnold, J. Organometallics 1997, 16, 1113.
9. 3SiOTf.
10. 1H NMR spectroscopy indicates the formation of multiple unidentified products.
11. 1H} NMR, and GC-MS.
12. Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
13. LaPointe, R. E.; Wolczanski, P. T.; Mitchell, J. J. Am. Chem. Soc. 1986, 108, 6382.
14. Deutscher, R. L.; Kepert, D. L. Inorg. Chim. Acta 1970, 4, 645.
15. van Asselt, A.; Burger, B. J.; Gibson, V. C.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 5347.
16. Crystallographic data for 5: colorless crystals, triclinic, P1̄, Z = 2, a = 10.6007(1) Å, b = 11.1973(1) Å, c = 16.8553(2) Å, a = 100.109-(1)°, β = 94.627(1)°, γ = 106.974(1)°, R = 0.041, GOF = 2.63.
17. (a) Parkin, G.; van Asselt, A.; Leahy, D. J.; Whinnery, L.; Hua, N. G.; Quan, R. W.; Henling, L. M.; Schaefer, W. P.; Santarsiero, B. D.; Bercaw, J. E. Inorg. Chem. 1992, 31, 82.
18. (b) For related Nb complexes see: Stewart, P. J.; Blake, A. J.; Mountford, P. Inorg. Chem. 1997, 36, 1982.
19. Ochiai, E. Aromatic Amine Oxides; Elsevier: Amsterdam, 1967.
20. 3 (18e) does not. This is consistent with the reactivity of many Schrock carbenes, in which formation of an adduct prior to reaction occurred only for carbene complexes with formal electron counts lower than 18e.
21. Katritzky, A. R.; Lagowski, J. M. Chemistry of the Heterocyclic N-Oxides; Academic Press: New York, 1971; p 258.
22. Breuer, E. Nitrones, Nitronates and Nitroxides; Wiley: Chichester, U.K., 1989; pp 139-311.
23. 1H} NMR and GC-MS.
24. The imine, tBuNCPh(Me), and 5 do not react at 45°C, ruling out a mechanism directly analogous to the pyridine N-oxide example, where 5 and tBuNCPh(Me) are initially formed but react further to eventually yield 14 and styrene.