Table of Contents
Journal of Inorganic Chemistry
Volume 2013 (2013), Article ID 149425, 6 pages
http://dx.doi.org/10.1155/2013/149425
Research Article

Computational Study on the Intramolecular Carbene-CO Coupling in M(CH2)(CO)3 Radicals (M = Co, Rh, Ir)

MTA-TKI Research Group for Selective Chemical Syntheses, Department of Inorganic Chemistry, János Szentágothai Research Center, University of Pécs, Ifjúság Útja 6, Pécs 7624, Hungary

Received 30 September 2013; Revised 3 December 2013; Accepted 4 December 2013

Academic Editor: Arturo Espinosa

Copyright © 2013 Gábor Tollár and Tamás Kégl. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. E. Leffler, The Reactive Intermediates of Organic Chemistry, Interscience Publishers, New York, NY, USA, 1956.
  2. T. T. Tidwell, “The first century of physical organic chemistry: a prologue,” Pure and Applied Chemistry, vol. 69, no. 2, pp. 211–213, 1997. View at Publisher · View at Google Scholar · View at Scopus
  3. C. Wentrup, W. Heilmayer, and G. Kollenz, “α-Oxoketenes—preparation and chemistry,” Synthesis, vol. 1994, no. 12, pp. 1219–1248, 1994. View at Publisher · View at Google Scholar
  4. T. T. Tidwell, “The first century of ketenes (1905–2005): the birth of a versatile family of reactive intermediates,” Angewandte Chemie, vol. 44, no. 36, pp. 5778–5785, 2005. View at Publisher · View at Google Scholar
  5. T. T. Tidwell, “Ketene chemistry after 100 years: ready for a new century,” European Journal of Organic Chemistry, vol. 2006, no. 3, pp. 563–576, 2006. View at Publisher · View at Google Scholar
  6. D. H. Paull, A. Weatherwax, and T. Lectka, “Catalytic, asymmetric reactions of ketenes and ketene enolates,” Tetrahedron, vol. 65, no. 34, pp. 6771–6803, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. H. Urtel, G. A. Bikzhanova, D. B. Grotjahn, and P. Hofmann, “Reversible carbon-carbon double bond cleavage of a ketene ligand at a single iridium(I) center: a theoretical study,” Organometallics, vol. 20, no. 18, pp. 3938–3949, 2001. View at Publisher · View at Google Scholar · View at Scopus
  8. N. Ungvári, E. Fördős, J. Balogh, T. Kégl, L. Párkányi, and F. Ungváry, “Triphenylphosphane-modified cobalt catalysts for the selective carbonylation of ethyl diazoacetate,” Organometallics, vol. 29, no. 7, pp. 3837–3851, 2010. View at Publisher · View at Google Scholar
  9. B. Barcs, L. Kollár, and T. Kégl, “Density functional study on the mechanism of nickel-mediated diazo carbonylation,” Organometallics, vol. 31, no. 23, pp. 8082–8097, 2012. View at Publisher · View at Google Scholar
  10. Z. Zhang, Y. Zhang, and J. Wang, “Carbonylation of metal carbene with carbon monoxide: generation of ketene,” ACS Catalysis, vol. 1, no. 11, pp. 1621–1630, 2011. View at Publisher · View at Google Scholar · View at Scopus
  11. W. I. Dzik, X. Xu, X. P. Zhang, J. N. H. Reek, and B. De Bruin, “‘Carbene radicals’ in CoII(por)-catalyzed olefin cyclopropanation,” Journal of the American Chemical Society, vol. 132, no. 31, pp. 10891–10902, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. H. Lu, W. I. Dzik, X. Xu, L. Wojtas, B. De Bruin, and X. P. Zhang, “Experimental evidence for cobalt(III)-carbene radicals: key intermediates in cobalt(II)-based metalloradical cyclopropanation,” Journal of the American Chemical Society, vol. 133, no. 22, pp. 8518–8521, 2011. View at Publisher · View at Google Scholar · View at Scopus
  13. N. D. Paul, H. Lu, X. P. Zhang, and B. de Bruin, “Carbene radicals in cobalt(II)-porphyrin-catalysed carbene carbonylation reactions; a catalytic approach to ketenes,” Chemistry, vol. 19, no. 39, pp. 12953–12958, 2013. View at Publisher · View at Google Scholar
  14. W. I. Dzik, J. N. H. Reek, and B. De Bruin, “Selective C–C coupling of Ir-ethene and Ir-carbenoid radicals,” Chemistry, vol. 14, no. 25, pp. 7594–7599, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. B. de Bruin, J. C. Russcher, and H. Grützmacher, “Spin density distribution in mononuclear Rh(0) complexes: a combined experimental and DFT study,” Journal of Organometallic Chemistry, vol. 692, no. 15, pp. 3167–3173, 2007. View at Publisher · View at Google Scholar
  16. W. I. Dzik, X. P. Zhang, and B. De Bruin, “Redox noninnocence of carbene ligands: carbene radicals in (Catalytic) C–C bond formation,” Inorganic Chemistry, vol. 50, no. 20, pp. 9896–9903, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. N. M. G. Franssen, A. J. C. Walters, J. N. H. Reek, and B. De Bruin, “Carbene insertion into transition metal-carbon bonds: a new tool for catalytic C–C bond formation,” Catalysis Science & Technology, vol. 1, pp. 153–165, 2011. View at Publisher · View at Google Scholar
  18. J. P. Perdew, K. Burke, and M. Ernzerhof, “Generalized gradient approximation made simple,” Physical Review Letters, vol. 77, no. 18, pp. 3865–3868, 1996. View at Publisher · View at Google Scholar · View at Scopus
  19. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., “Gaussian 09 Revision C. 01,” Gaussian Inc., Wallingford, Conn, USA, 2009.
  20. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, and H. Preuss, “Energy-adjusted ab initio pseudopotentials for the second and third row transition elements,” Theoretica Chimica Acta, vol. 77, no. 2, pp. 123–141, 1990. View at Publisher · View at Google Scholar
  21. A. Schaefer, C. Huber, and R. Ahlrichs, “Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr,” Journal of Chemical Physics, vol. 100, no. 8, p. 5829, 1994. View at Publisher · View at Google Scholar
  22. C. Gonzalez and H. B. Schlegel, “An improved algorithm for reaction path following,” The Journal of Chemical Physics, vol. 90, no. 4, pp. 2154–2161, 1989. View at Publisher · View at Google Scholar · View at Scopus
  23. E. D. Glendening, J. K. Badenhoop, A. E. Reed et al., “NBO 5.0,” Theoretical Chemistry Institute, University of Wisconsin, Madison, Wis, USA, 2001.
  24. T. A. Keith, AIMAll (Version 13. 05. 06), TK Gristmill Software, Overland Park, Kan, USA, 2013, http://aim.tkgristmill.com/.
  25. M. Cossi, N. Rega, G. Scalmani, and V. Barone, “Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model,” Journal of Computational Chemistry, vol. 24, no. 6, pp. 669–681, 2003. View at Publisher · View at Google Scholar · View at Scopus