New cascade processes on group 6 fischer-type carbene complexes: Cyclopropanation and metathesis reactions

Organic Letters

Volumn 9, Issue 21, 2007, Pages 4143-4146

  Barluenga, José ^a   Andina, Facundo ^a   Aznar, Fernando ^a   Valdé, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35548983584     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701604g     Document Type: Article

References (36)

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23. Some representative examples of metathesis processes of Fischer carbene complexes with electron-rich olefins: (a) Fischer, E. O.; Dötz, K. H. Chem. Ber. 1972, 105, 3966.
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28. Calculations were carried out with the Gaussian03 package of programs (see the Supporting Information for the complete reference).
29. Geometry optimizations were carried out employing the LANL2DZ ECP for W and Cr and the 6-31G(d) basis set for the rest of the atoms. Single point energy calculations at the stationary points were carried out employing the 6-311++G** basis set for the light elements and again the LANL2DZ basis set for the metals. Solvation free energy was calculated employing the SRCF PCM model. See the Supporting Information for further details.
30. For some selected examples on DFT calculations on group 6 Fischer carbene complexes see: (a) Gleichmann, M. M.; Dötz, K. H.; Hess, B. A. J. Am. Chem. Soc 1996, 118, 10551.
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34. (e) Fernández, I.; Cossío, F. P.; Sierra, M. A. Organometallics 2007, 26, 3010 and references cited therein.
35. Similar results have been previously reported for metathesis reactions of simpler tungsten carbene complexes: Tlenkopatchev, M.; Fomine, S. J. Organomet. Chem. 2001, 630, 157.
36. -1 for the bond dissociation potential energy for the CO ligand. However, to determine the activation free energy of the CO dissociation in solution is not straightforward, due to the overestimation of the entropie contributions in ligand dissociation reactions. See: Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457. For this reason, a free energy comparison between both reaction pathways has not been attempted. See the Supporting Information for further details.