The reactivity of Mo(PMe3)6 towards heterocyclic nitrogen compounds: Transformations relevant to hydrodenitrogenation

Journal of the American Chemical Society

Volumn 124, Issue 46, 2002, Pages 13658-13659

  Zhu, Guang ^a   Tanski, Joseph M ^a   Churchill, David G ^a   Janak, Kevin E ^a   Parkin, Gerard ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FOSSIL FUEL; HETEROCYCLIC COMPOUND; MOLYBDENUM; NITROGEN DERIVATIVE; PHOSPHORUS DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH TEMPERATURE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0037146044     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028512w     Document Type: Article

References (30)

1. (a) Angelici, R. J. Polyhedron 1997, 16, 3073.
2. (b) Weller, K. J.; Fox, P. A.; Gray, S. D.; Wigley, D. E. Polyhedron 1997, 16, 3139.
3. (c) Bianchini, C.; Meli, A.; Vizza, F. Eur. J. Inorg. Chem. 2001, 43.
4. (d) Laine, R. M. Catal. Rev. - Sci. Eng. 1983, 25, 459.
5. (e) Sanchez-Delgado, R. A. Organometallic Modelling of the Hydrode Sulfurization and Hydrodenitrogenation Reactions; Kluwer Academic Publishers: Boston, 2002.
6. Murphy, V. J.; Parkin, G. J. Am. Chem. Soc. 1995, 117, 3522.
7. Janak, K. E.; Tanski, J. M.; Churchill, D. G.; Parkin, G. J. Am. Chem. Soc. 2002, 124, 4182.
8. 4(OAr)H derivatives, see: (a) Hascall, T.; Murphy, V. J.; Parkin, G. Organometallics 1996, 15, 3910. (b) Hascall, T.; Murphy, V. J.; Janak, K. E.; Parkin, G. J. Organomet. Chem. 2002, 652, 37.
9. 4(OAr)H derivatives, see: (a) Hascall, T.; Murphy, V. J.; Parkin, G. Organometallics 1996, 15, 3910. (b) Hascall, T.; Murphy, V. J.; Janak, K. E.; Parkin, G. J. Organomet. Chem. 2002, 652, 37.
10. 3 have been determined by X-ray diffraction. See Supporting Information.
11. 1-indolyl complexes, see: (a) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385. (b) Johnson, T. J.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 3182. (c) Chen, S.; Noll, B. C.; Peslherbe, L.; Rakowski DuBois, M. Organometallics 1997, 16, 1089. (d) Ladipo, F. T.; Merola, J. S. Inorg. Chem. 1990, 29, 4172.
12. 1-indolyl complexes, see: (a) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385. (b) Johnson, T. J.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 3182. (c) Chen, S.; Noll, B. C.; Peslherbe, L.; Rakowski DuBois, M. Organometallics 1997, 16, 1089. (d) Ladipo, F. T.; Merola, J. S. Inorg. Chem. 1990, 29, 4172.
13. 1-indolyl complexes, see: (a) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385. (b) Johnson, T. J.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 3182. (c) Chen, S.; Noll, B. C.; Peslherbe, L.; Rakowski DuBois, M. Organometallics 1997, 16, 1089. (d) Ladipo, F. T.; Merola, J. S. Inorg. Chem. 1990, 29, 4172.
14. 1-indolyl complexes, see: (a) Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallics 1994, 13, 385. (b) Johnson, T. J.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 3182. (c) Chen, S.; Noll, B. C.; Peslherbe, L.; Rakowski DuBois, M. Organometallics 1997, 16, 1089. (d) Ladipo, F. T.; Merola, J. S. Inorg. Chem. 1990, 29, 4172.
15. 5-indolyl complexes, see: Ji, L.-N.; Kershner, D. L.; Rerek, M. E.; Basolo, F. J. Organomet. Chem. 1985, 296, 83 and references therein.
16. See, for example: Chen, S.; Carperos, V.; Noll, B.; Swope, R. J.; Rakowski DuBois, M. Organometallics 1995, 14, 1221.
17. 6-indolyl complex see ref 8.
18. An alternative description is that it there is a contribution from a cyclohexadienyl resonance structure. See, for example: (a) Helling, J. F.; Hendrickson, W. A. J. Organomet. Chem. 1977, 141, 99. (b) Johnson, J. W.; Treichel, P. M. J. Am. Chem. Soc. 1977, 99, 1427.
19. An alternative description is that it there is a contribution from a cyclohexadienyl resonance structure. See, for example: (a) Helling, J. F.; Hendrickson, W. A. J. Organomet. Chem. 1977, 141, 99. (b) Johnson, J. W.; Treichel, P. M. J. Am. Chem. Soc. 1977, 99, 1427.
20. 3 is known. See: Nesmeyanov, A. N.; Ustynyuk, N. A.; Thoma, T.; Prostakov, N. S.; Soldatenkov, A. T.; Pleshakov, V. G.; Ustynyuk, Yu. A.; Trifonova, O. I.; Oprunenko, Yu, F. J. Organomet. Chem. 1982, 231, 5.
21. -1; AS = 24.6(11) eu.
22. -1 and ΔS‡ = -8(3) eu.
23. For inter-ring haptotropic shifts in bicyclic systems, see: Oprunenko, Yu, F. Russ. Chem. Rev. 2000, 69, 683 and references therein.
24. 4H as an intermediate.
25. See, for example: Riley, P. N.; Parker, J. R.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1999, 18, 3579 and references therein.
26. 6-carbazolyl complexes, see refs 10a and 11.
27. Morris, R. H.; Ressner, J. M. J. Chem. Soc., Chem. Commun. 1983, 909.
28. 6-coordination via the carbocyclic ring are known (ref 1c). See, for example: Fish, R. H.; Fong, R. H.; Tran, A.; Baralt, E. Organometallics 1991, 10, 1209 and references therein.
29. 1-coordination. See, for example: Cotton, F. A.; Felthouse, T. R. Inorg. Chem. 1981, 20, 600.
30. For homogeneous catalytic hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline, see: Bianchini, C.; Barbaro, P.; Macchi, M.; Meli, A.; Vizza, F. Helv. Chim. Acta 2001, 84, 2895 and references therein.