Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources

New Journal of Chemistry

Volumn 26, Issue 10, 2002, Pages 1296-1303

  Cole, Marcus L ^a   Jones, Cameron ^b   Junk, Peter C ^a  

^a MONASH UNIVERSITY   (Australia)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,1,2,2,2 HEXACHLOROETHANE; 1,2 DIBROMOETHANE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL) 2 BROMOIMIDAZOLIUM BROMIDE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL) 2 CHLOROIMIDAZOLIUM CHLORIDE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL) 4,5 DIBROMOIMIDAZOL 2 YLIDENE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL)IMIDAZOL 2 YLIDENE; 1,3 BIS(2,4,6 TRIMETHYLPHENYL)IMIDAZOLIUM BROMIDE; ALKENE DERIVATIVE; ALUMINIUM TRICHLORIDE; ALUMINUM DERIVATIVE; BENZENE; BROMINE DERIVATIVE; CARBENOID; CARBON TETRABROMIDE; HALIDE; HALOGEN; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0036398896     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b204422f     Document Type: Article

References (48)

1. A. J. Arduengo III, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1991, 113, 361.
2. D. Bourissou, O. Guerret, F. P. Gabbaï and G. Bertrand, Chem. Rev., 2000, 100, 39.
3. A. M. Magill, D. S. McGuiness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. P. White, D. J. Williams, A. H. White and B. W. Skelton, J. Organomet. Chem., 2001, 617-618, 546.
4. L. Jafarpour and S. P. Nolan, J. Organomet. Chem, 2001, 617-618, 17.
5. A. A. D. Tulloch, A. A. Danopoulos, R. P. Tooze, S. M. Cafferkey, S. Kleinhenz and M. B. Hursthouse, Chem. Commun., 2000, 1247.
6. D. S. McGuiness and K. J. Cavell, Organometallics, 2000, 19, 741.
7. J. K. Huang, E. D. Stevens, S. P. Nolan and J. L. Petersen, J. Am. Chem. Soc., 1999, 121, 2674.
8. C. J. Carmalt and A. H. Cowley, Adv. Inorg. Chem., 2000, 50, 1.
9. C. Jones, Chem. Commun., 2001, 2293.
10. S. J. Black, D. E. Hibbs, M. B. Hursthouse, C. Jones, K. M. A. Malik and N. A. Smithies, J. Chem. Soc., Dalton Trans., 1997, 4313.
11. M. L. Cole, A. J. Davies and C. Jones, J. Chem. Soc., Dalton Trans., 2001, 2451.
12. C. D. Abernethy, M. L. Cole and C. Jones, Organometallics, 2000, 19, 4852.
13. C. D. Abernethy, R. J. Baker, M. L. Cole, A. J. Davies and C. Jones, Transition Met. Chem., in press.
14. D. E. Hibbs, M. B. Hursthouse, C. Jones and N. A. Smithies, Main Group Chem., 1998, 2, 293.
15. R. J. Baker, M. L. Cole, C. Jones and M. F. Mahon, J. Chem. Soc., Dalton Trans., 2002, 1992.
16. N. Kuhn, T. Kratz and G. Henkel, J. Chem. Soc., Chem. Commun., 1993, 1778.
17. A. J. Arduengo III, M. Kline, J. C. Calabrese and F. Davidson, J. Am. Chem. Soc., 1991, 113, 9704.
18. A. J. Arduengo III, M. Tamm and J. C. Calabrese, J. Am. Chem. Soc., 1994, 116, 3625.
19. A. J. Arduengo III, F. Davidson, H. V. R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall and T. K. Prakasha, J. Am. Chem. Soc., 1997, 119, 12 742.
20. 2 has been used: (a) J. Huang, H.-J. Schanz, E. D. Stevens and S. P. Nolan, Organometallics, 1999, 18, 2370; (b) W. J. Oldham, S. M. Oldham, B. L. Scott, K. D. Abney, W. H. Smith and D. A. Costa, Chem. Commun., 2001, 1348; (c) A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236; (d) A. J. Arduengo, F. Davidson, R. Krafczyk, W. J. Marshall and R. Schmutzler, Monatsh. Chem., 2000, 131, 251; (e) A. J. Arduengo, R. Krafzyck, R. Schmutzler, W. Mahler and W. J. Marshall, Z. Anorg. Allg. Chem., 1999, 625, 1813
21. 2 has been used: (a) J. Huang, H.-J. Schanz, E. D. Stevens and S. P. Nolan, Organometallics, 1999, 18, 2370; (b) W. J. Oldham, S. M. Oldham, B. L. Scott, K. D. Abney, W. H. Smith and D. A. Costa, Chem. Commun., 2001, 1348; (c) A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236; (d) A. J. Arduengo, F. Davidson, R. Krafczyk, W. J. Marshall and R. Schmutzler, Monatsh. Chem., 2000, 131, 251; (e) A. J. Arduengo, R. Krafzyck, R. Schmutzler, W. Mahler and W. J. Marshall, Z. Anorg. Allg. Chem., 1999, 625, 1813
22. 2 has been used: (a) J. Huang, H.-J. Schanz, E. D. Stevens and S. P. Nolan, Organometallics, 1999, 18, 2370; (b) W. J. Oldham, S. M. Oldham, B. L. Scott, K. D. Abney, W. H. Smith and D. A. Costa, Chem. Commun., 2001, 1348; (c) A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236; (d) A. J. Arduengo, F. Davidson, R. Krafczyk, W. J. Marshall and R. Schmutzler, Monatsh. Chem., 2000, 131, 251; (e) A. J. Arduengo, R. Krafzyck, R. Schmutzler, W. Mahler and W. J. Marshall, Z. Anorg. Allg. Chem., 1999, 625, 1813
23. 2 has been used: (a) J. Huang, H.-J. Schanz, E. D. Stevens and S. P. Nolan, Organometallics, 1999, 18, 2370; (b) W. J. Oldham, S. M. Oldham, B. L. Scott, K. D. Abney, W. H. Smith and D. A. Costa, Chem. Commun., 2001, 1348; (c) A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236; (d) A. J. Arduengo, F. Davidson, R. Krafczyk, W. J. Marshall and R. Schmutzler, Monatsh. Chem., 2000, 131, 251; (e) A. J. Arduengo, R. Krafzyck, R. Schmutzler, W. Mahler and W. J. Marshall, Z. Anorg. Allg. Chem., 1999, 625, 1813
24. 2 has been used: (a) J. Huang, H.-J. Schanz, E. D. Stevens and S. P. Nolan, Organometallics, 1999, 18, 2370; (b) W. J. Oldham, S. M. Oldham, B. L. Scott, K. D. Abney, W. H. Smith and D. A. Costa, Chem. Commun., 2001, 1348; (c) A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236; (d) A. J. Arduengo, F. Davidson, R. Krafczyk, W. J. Marshall and R. Schmutzler, Monatsh. Chem., 2000, 131, 251; (e) A. J. Arduengo, R. Krafzyck, R. Schmutzler, W. Mahler and W. J. Marshall, Z. Anorg. Allg. Chem., 1999, 625, 1813
25. N. Kuhn, J. Fahl, R. Fawzi, C. Maichle-Mossmer and M. Steimann, Z. Naturforsch., B, 1998, 53, 720.
26. T. Isobe and T. Ishikawa, J. Org. Chem., 1999, 64, 5832 and references cited therein.
27. The Strengths of Chemical Bonds, T. L. Cottrell, Butterworth, US, 2nd edn., 1958.
28. Some Thermodynamic Aspects of Inorganic Chemistry, D. A. Johnson, Cambridge University Press, UK, 2nd edn., 1982.
29. A. J. Arduengo III, S. F. Gamper, M. Tamm, J. C. Calabrese, F. Davidson and H. A. Craig, J. Am. Chem. Soc., 1995, 117, 572.
30. The Hydrogen Bond, ed. P. Schuster, G. Zundel and C. Sandorfy, Amsterdam, Holland, vol. 2, 1976.
31. Tables of Interatomic Distances and Configurations in Molecules and Ions, ed. L. E. Sutton, Chemical Society Publications, UK, 1965.
32. C. A. Ilioudis, K. S. B. Hancock, D. Georganopoulou and J. W. Steed, New J. Chem., 2000, 787.
33. Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. Garcia-Espana, Wiley-VCH, New York, 1997.
34. F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609.
35. B. Dietrich, Pure Appl. Chem., 1993, 65, 1457.
36. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, Germany, 1995.
37. J. L. Atwood, K. T. Holman and J. W. Steed, Chem. Commun., 1996, 1401.
38. E. Fluck, H. G. Heumann, Periodic Table of the Elements, VCH, Weinheim, Germany, 1991.
39. J. Emsley, The Elements, Oxford University Press, Oxford, UK, 1989.
40. A. J. Arduengo III, H. V. R. Dias, R. L. Harlow and M. Kline, J. Am. Chem. Soc., 1992, 114, 5530.
41. M. K. Denk and J. M. Rodezno, J. Organomet. Chem., 2000, 608, 122.
42. C. Hardacre, J. D. Holbrey and S. E. J. McMath, Chem. Commun., 2001, 367.
43. K. Biradha and M. J. Zaworotko, J. Am. Chem. Soc., 1998, 120, 6431.
44. G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, UK, 1999.
45. R. H. Blessing, Acta Crystallogr., Sect A, 1995, 51, 33.
46. G. M. Sheldrick, SHELXL-97, University of Göttingen, Germany 1997.
47. L. J. Barbour, X-SEED Crystallographic Interface, University of Missouri-Columbia, 1999.
48. T. Welton, Chem. Rev., 1999, 99, 2071.