A new paradigm in N-heterocyclic carbenoid ligands

Journal of Organometallic Chemistry

Volumn 690, Issue 24-25, 2005, Pages 6210-6216

  Page, Philip C Bulman ^a   Buckley, Benjamin R ^a   Christie, Steven D R ^a   Edgar, Mark ^a   Poulton, Andrew M ^a   Elsegood, Mark R J ^a   McKee, Vickie ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

Asymmetry; Atropoisomerism; Benzimidazolylidene; Carbene; Chirality; Imidazolylidene

Indexed keywords

COMPLEXATION; HYDROPHOBIC CHROMATOGRAPHY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ASYMMETRY; ATROPOISOMERISM; BENZIMIDAZOLYLIDENE; CARBENES; CHIRALITY; IMIDAZOLYLIDENE;

ORGANOMETALLICS;

EID: 27744551051     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.09.015     Document Type: Article

References (20)

1. For a recent review, see: A.J. Arduengo Acc. Chem. Res. 32 1999 913
2. W.A. Herrmann, L.J. Goossen, C. Köcher, and G.R.J. Artus Angew. Chem., Int. Ed. Engl. 35 1996 2805
3. W.A. Herrmann, L.J. Goossen, G.R.J. Artus, and C. Köcher Organometallics 16 1997 2472
4. J. Seiders, D.W. Ward, and R.H. Grubbs Org. Lett. 3 2001 3225
5. For a recent review, see: M.C. Perry, and K. Burgess Tetrahedron: Asymmetry 14 2003 951
6. J.J. Van Veldhuizen, J.E. Campbell, R.E. Giudici, and A.H. Hoveyda J. Am. Chem. Soc. 127 2005 6877
7. C. Bolm, T. Focken, and G. Raabe Tetrahedron: Asymmetry 14 2003 1733
8. H. Seo, H. Park, B.Y. Kim, J.H. Lee, S.U. Son, and Y.K. Chung Organometallics 22 2003 618
9. F.M. Rivas, U. Riaz, A. Giessert, J.A. Smulik, and S.T. Diver Org. Lett. 3 2001 2673
10. S. Gründemann, M. Albrecht, A. Kovacevic, J.W. Faller, and R.H. Crabtree J. Chem. Soc., Dalton Trans. 10 2002 2163
11. 2). Absolute structure parameter -0.06(3). Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 279711 for compound 1.
12. R.J. Abraham, J. Fisher, and P. Loftus Introduction to NMR Spectroscopy 1988 Wiley Chichester
13. Spartan '04 for Macintiosh, Wavefunction Inc., Irvine, CA.
14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian Inc. Wallingford, CT
15. For chelating carbene complexes that are cis, see: W.A. Herrmann, M. Elison, J. Fischer, C. Kocher, and G.R.J. Artus Angew. Chem., Int. Ed. Engl. 34 1995 2371
16. M.G. Gardiner, W.A. Herrmann, C.P. Reisinger, J. Schwarz, and M. Spiegler J. Organomet. Chem. 572 1999 239
17. W.A. Herrmann, J. Schwarz, and M.G. Gardiner Organometallics 18 1999 4082
18. L. Jafarpour, J. Huang, E.D. Stevens, and S.P. Nolan Organometallics 18 1999 3760 18
19. A preliminary structural determination was performed for compound 2. Although the basic connectivity has been established unequivocally, unresolved twinning problems preclude the full reporting of this structure at the present time.
20. A.M. Poulton, S.D.R. Christie, R. Fryatt, S.H. Dale, M.R.J. Elsegood, and D.M. Andrews Synlett 2004 2103