Synthesis and characterization of new ruthenium-based olefin metathesis catalysts coordinated with bidentate Schiff-base ligands

Organometallics

Volumn 17, Issue 16, 1998, Pages 3460-3465

  Chang, Sukbok ^a   Jones II, LeRoy ^a   Wang, Chunming ^a   Henling, Lawrence M ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001645448     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970910y     Document Type: Article

References (36)

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2. For representative examples, see: (a) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A. Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 9.3. (b) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, CA, 1997.
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5. For representative examples, see: (a) Novak, B. M.; Risse, W.; Grubbs, R. H. Adv. Polymer. Sci. 1992, 102, 47. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552. (c) Hashimi, A. S. K. J. Prakt. Chem. 1997, 339, 195-199.
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28. For recent examples of chiral ruthenium Schiff-base complexes in asymmetric reactions, see: (a) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, K. N. Tetrahedron: Asymmetry 1993, 4, 1693-1701. (b) Chuard, T.; Gretillat, F.; Bernauer, K. Chimia 1993, 47, 215-217. (c) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, A. K. J. Mol. Catal. A 1997, 120, 101-108.
29. For recent examples of chiral ruthenium Schiff-base complexes in asymmetric reactions, see: (a) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, K. N. Tetrahedron: Asymmetry 1993, 4, 1693-1701. (b) Chuard, T.; Gretillat, F.; Bernauer, K. Chimia 1993, 47, 215-217. (c) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, A. K. J. Mol. Catal. A 1997, 120, 101-108.
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35. 3-Methyl-5-nitrosalicylaldehyde was prepared in the following manner. o-Cresol was treated with anhydrous stannic chloride, paraformaldehyde, 2,6-lutidine, and toluene to afford 3-methylsalicylaldehyde in 40% yield. The corresponding aldehyde was then nitrated using glacial acetic acid and concentrated nitric acid to afford the title compound in 97% yield.
36. 2,6-Diisopropyl-4-nitrobenzene was prepared in an analogous manner to that found in Wepster, B. M. Recl. Trav. Chim. 1954, 73, 809-818. 2,6-Diisopropylaniline was protected as the sulfonamide using tosyl chloride, pyridine, and dichloromethane in 97% yield. The corresponding sulfonamide was then nitrated using concentrated nitric acid, water, acetic anhydride, and sodium nitrite in 53% yield. Deprotection of the amine was accomplished using a 10:1 mixture of concentrated sulfuric acid:water to afford the title compound in quantitative yields.