Aryl isocyanate, carbodiimide, and isocyanide prepared from carbon dioxide. A metathetical group-transfer tale involving a titanium-imide zwitterion

Inorganic Chemistry

Volumn 45, Issue 2, 2006, Pages 487-489

  Kilgore, Uriah J ^a   Basuli, Falguni ^a   Huffman, John C ^a   Mindiola, Daniel J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544474328     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic052065e     Document Type: Article

References (40)

1. (a) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207-2221.
2. (b) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747-764.
3. (a) Arakawa, H.; et al. Chem. Rev. 2001, 101, 953-996.
4. (b) Gibson, D. H. Chem. Rev. 1996, 96, 2063-2095.
5. (c) Dell'Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857-3898.
6. (a) Byrne, C. M.; Allen, S. D.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2004, 126, 11404-11405.
7. (b) Sita, L. R.; Babcock, J. R.; Xi, R. J. Am. Chem. Soc. 1996, 118, 10912-10913.
8. (c) Wannagat, U.; Kuckertz, H.; Kruger, C.; Pump, J. Z. Anorg. Allg. Chem. 1964, 333, 54-61.
9. (d) Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2001, 123, 2895-2896.
10. (e) Takimoto, M.; Shimizu, K.; Mori, M. Org. Lett. 2001, 3, 3345-3347.
11. (f) Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. J. Org. Chem. 1999, 64, 3975-3978.
12. (g) Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2004, 126, 8590-8590.
13. Basuli, F.; Clark, R. L.; Bailey, B. C.; Brown, D.; Huffman, J. C.; Mindiola, D. J. Chem. Commun. 2005, 2250-2252.
14. See the Supporting Information for complete experimental and relevant crystallographic details.
15. (a) Sánchez-Nieves, J.; Frutos, L. M.; Royo, P.; Castaño, O.; Herdtweck, E. Organometallics 2005, 24, 2004-2007.
16. (b) Vidovic, D.; Moore, J A.; Jones, J. N.; Cowley, A. H. J. Am. Chem. Soc. 2005, 127, 4566-4567.
17. int = 7.48%) with I > 2σ(I) (yellow needle, 0.30 x 0.12 x 0.06 mm, 27.43° ≥ Θ ≥ 3.80°). A disordered diethyl ether is present in the cell.
18. (a) Blake, R. E., Jr.; Antonelli, D. M.; Henling, L. M.; Schaefer, W. P.; Hardcastle, K. I.; Bercaw, J. E. Organometallics 1998, 17, 718-725.
19. (b) Boyd, C. L.; Clot, E.; Guiducci, A. E.; Mountford, P. Organometallics 2005, 24, 2368-2385.
20. (c) Swallow, D.; McInnes, J. M.; Mountford, P. Dalton Trans. 1998, 2253-2260.
21. (d) Dubberley, S. R.; Friedrich, A.; Willman, D. A.; Mountford, P.; Radius, U. Chem. - Eur. J. 2003, 9, 3634-3654.
22. (e) Boyd, C. L.; Toupance, T.; Tyrrell, B. R.; Ward, B. D.; Wilson, C. R.; Cowley, A. R.; Mountford, P. Organometallics 2005, 24, 309-330.
23. (f) Boyd, C. L.; Clot, E.; Guiducci, A. E.; Mountford, P. Organometallics 2005, 24, 2347-2367.
24. (g) Molina, P.; Alajarin, M.; Arques, A. Synthesis 1982, 596-597.
25. (h) Hsu, S.-H.; Chang, J.-C.; Lai, C.-L.; Hu, C.-H.; Lee, H. M.; Lee, G.-H.; Peng, S.-M.; Huang, J.-H. Inorg. Chem. 2004, 43, 6786-6792.
26. (i) Royo, R.; Sánchez-Nieves, J. J. Organomet. Chem. 2000, 597, 61-68.
27. Guiducci, A. E.; Cowley, A. R.; Skinner, M. E. G.; Mountford, P. Dalton Trans. 2001, 1392-1394.
28. Blake, A. J.; McInnes, J. M.; Mountford, P.; Nikonov, G. I.; Swallow, D.; Watkin, D. J. Dalton Trans. 1999, 379-392.
29. (a) Basuli, F.; Bailey, B. C.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2003, 125, 6052-6053.
30. (b) Basuli, F.; Bailey, B. C.; Watson, L. A.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. Organometallics 2005, 24, 1886-1906.
31. int = 15.47%) with I > 2σ(I) (yellow prism, 0.25 x 0.05 x 0.05 mm, 27.57° ≥ Θ ≥ 2.04°). In addition to the molecule of interest, there is a region of disordered solvent that could not be resolved. The latter was modeled as a series of partial occupancy carbon atoms. All nonsolvent hydrogen atoms were located in subsequent Fourier maps and included as isotropic contributors in the final cycles of refinement. Solvent hydrogen atoms were ignored.
32. 2 under the same conditions.
33. (a) DeLaet, D. L.; del Rosario, R.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1987, 109, 754-758.
34. (b) Babcock, J. R.; Sita, L. R. J. Am. Chem. Soc. 1998, 120, 5585-5586.
35. (a) Wang, H.; Chan, H.-S.; Xie, Z. Organometallics 2005, 24, 3772-3779.
36. (b) Lee, S. Y.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 6396-6406.
37. int = 6.06%) with I > 2σ(I) (orange cleaved fragment, 0.30 x 0.30 x 0.30 mm, 30.04° ≥ Θ ≥ 2.12°).
38. Baldwin, J. E.; Bottaro, J. C.; Roirdan, P. D.; Derome, A. E. J. Chem. Soc., Chem. Commun. 1982, 942-943.
39. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-6825.
40. Dean, D. C.; Wallace, M. A.; Marks, T. M.; Melillo, D. G. Tetrahedron Lett. 1997, 38, 919-922.