Transition-metal-catalyzed imine metathesis

Organometallics

Volumn 16, Issue 25, 1997, Pages 5381-5383

  Cantrell, Gidget K ^a   Meyer, Tara Y ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009837108     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9708889     Document Type: Article

References (30)

1. For reviews of olefin metathesis see: (a) Grubbs, R. H.; Tumas, W. Science 1989, 243, 907. (b) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (c) Amass, A. J. In New Methods of Polymer Synthesis; Ebdon, J. R., Ed.; Chapman and Hall: New York, 1991; p 76.
2. For reviews of olefin metathesis see: (a) Grubbs, R. H.; Tumas, W. Science 1989, 243, 907. (b) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (c) Amass, A. J. In New Methods of Polymer Synthesis; Ebdon, J. R., Ed.; Chapman and Hall: New York, 1991; p 76.
3. For reviews of olefin metathesis see: (a) Grubbs, R. H.; Tumas, W. Science 1989, 243, 907. (b) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (c) Amass, A. J. In New Methods of Polymer Synthesis; Ebdon, J. R., Ed.; Chapman and Hall: New York, 1991; p 76.
4. Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801-10802.
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6. Toth, G.; Pinter, I.; Messmer, A. Tetrahedron Lett. 1974, 9, 735-738.
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15. (a) Jolly, M.; Mitchell, J. P.; Gibson, V. C. J. Chem. Soc., Dalton Trans. 1992, 1329-1330.
16. (b) Nugent, W. A. Inorg. Chem. 1983, 22, 965-969.
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19. (e) Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc., Chem. Commun. 1978, 579-580.
20. Dillon, K. B.; Gibson, V. C.; Sequeira, L. J. J. Am. Chem. Soc., Chem. Commun. 1995, 2429-2430.
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22. Cantrell, G. K.; Meyer, T. Y. Chem. Commun. 1997, 1551-1552.
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24. Imines were prepared by condensation of the parent aldehyde and amine in benzene over molecular sieves, followed by purification by vacuum distillation. The procedure was analogous to that described for a different imine in: Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1986; Vol. II, p 302.
25. CH= 8.6 Hz). Note: both 5 and 6 have been prepared independently for comparison.
26. Jolly, M.; Mitchell, J. P.; Gibson, V. C. J. Chem. Soc., Dalton Trans. 1992, 1331-1332.
27. 1H spectrum due to accidental overlap of imine resonances.
28. A slight excess of 3 (16 equiv) over 4 (14 equiv) was present in the NMR tube.
29. Catalyst 1a reached equilibrium in ∼5 h, while 2 required ∼10 h. The difference in completion times is attributed to the continued initiation of the more reactive 1a to produce additional active catalyst.
30. TOF = (equiv of product imine at equilibrium)/(equiv of active catalyst)(time to equilibrium) = ∼15/(0.5 (Mo))(10 h).