A convenient method for removing all highly-colored byproducts generated during olefin metathesis reactions

Organic Letters

Volumn 2, Issue 9, 2000, Pages 1259-1261

  Paquette, Leo A ^a   Schloss, Jeffrey D ^a   Efremov, Ivan ^a   Fabris, Fabrizio ^a   Gallou, Fabrice ^a   Méndez Andino, José ^a   Yang, Jiong ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001412617     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000036w     Document Type: Article

References (32)

1. Olefin Metathesis and Metathesis Polymerization; Ivin, K. J., Mol, J. C., Academic Press: New York, 1997.
2. Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998.
3. For recent reviews, consult: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
4. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
5. (c) Fürstner, A. Topics Catal. 1997, 4, 285.
6. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
7. (e) Pariya, C.; Jayaprakash, K. N.; Sarkar, A. Coord. Chem. Rev. 1998, 168, 1.
8. (f) Randall, M. L.; Snapper, M. L. J. Mol. Catal. A: Chem. 1998, 133, 29.
9. (g) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
10. (h) Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1.
11. (i) Wright, D. L. Curr. Org. Chem. 1999, 3, 211.
12. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
13. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am Chem. Soc. 1992, 114, 3974.
14. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
15. Fu, G.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426.
16. (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
17. (b) Callam, C. S.; Lowary, T. L. Org. Lett. 2000, 2, 167.
18. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137.
19. The prices quoted in the 1999-2001 Strem Chemical Inc. catalog for tris(hydroxymetriyl)phosphine are $40/1 g and $560/25 g.
20. (a) Criegee, R. In Oxidation in Organic Chemistry; Wiberg K. B., Ed.; Academic Press: New York, 1965; Part A, pp 277-366.
21. (b) Butler, R. N. In Synthetic Reagents; Pizey, J. S., Ed.; Ellis Horwood Limited: Chichester, 1977; Vol. 3, pp 277-419.
22. (c) Rubottom, G. M. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York 1982: Part D, pp 1-145.
23. (d) Mihailovic, M. L.; Cekovic, Z.; Lorenc, L. In Svnth. Oxid. Met. Compd.; Mijs, W. J., DeJonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; pp 741-816.
24. (a) Barborak, J. C.; Pettit, R. J. Am. Chem. Soc. 1967, 89, 3080.
25. (b) Merk, W.; Pettit, R. J. Am. Chem. Soc. 1967, 89, 4787.
26. (c) Masamune, S.; Nakamura, N.; Spadaro, J. J. Am. Chem. Soc. 1975, 97, 918.
27. (d) Brener, L.; McKennis, J. S.; Pettit, R. Org. Synth. 1976, 55, 43.
28. Berka, A.; Dvorak, V.; Nemec, I.; Zyka, J. J. Electroanal. Chem. 1952, 4, 150.
29. Milazzo, G.; Caroli, S.; Sharma, V. K. Tables of Standard Electrode Potentials; John Wiley and Sons: New York, 1978; pp 350-354.
30. Only in one or two instances was an increase in solvent polarity required to rinse off the more polar product(s). The use of ethyl acetate for this purpose did cause a very modest amount of pale yellow color to leach out.
31. Each carefully weighed RCM product was added to 10 mL of high purity concentrated nitric acid and diluted with deionized water to a total volume of 100 mL after thorough mixing and dissolution. Two separate aliquots of each sample were prepared to assess potential inhomogeneity of the solid sample (none was found). Calibration standards (1, 5, 10, 50, 100, 500 ng/mL) of Ru and Pb were made by serial dilution of μg/mL standard solutions (CPI International, traceable to NIST standards) in 10% v/v nitric acid. A blank was made from 10% v/v nitric acid. A Perkin-Elmer Sciex ELAN 6000 Inductively Coupled Plasma-Mass Spectrometer was used for all analyses. Signals for four Ru isotopes (99, 101, 102, and 104) and three Pb isotopes (206, 207, 208) were measured. Three replicate measurements were made for each standard and sample. Samples with measured solution concentrations greater than 500 ng/mL were diluted by a factor of 20 in 10 v/v nitric acid and rerun to be certain that the results were within the range of concentrations for the calibration standards.
32. 2, a very insoluble solid is formed. Filtration of such solutions through silica gel according to the usual workup gives filtrates entirely devoid of phosphine, lead salt, or any other detectable residue.