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http://dx.doi.org/10.5012/jkcs.2004.48.1.028

Reaction of Phosphorus Ylides with Carbonyl Compounds in Supercritical Carbon Dioxide  

Jeong, Kyung-Il (Department of Chemistry and Institute of Natural Sciences, Yeungnam University)
Kim, Hak-Do (Department of Chemistry and Institute of Natural Sciences, Yeungnam University)
Shim, Jae-Jin (School of Chemical Engineering and Technology, Yeungnam University)
Ra, Choon-Sup (Department of Chemistry and Institute of Natural Sciences, Yeungnam University)
Publication Information
Journal of the Korean Chemical Society / v.48, no.1, 2004 , pp. 28-32 More about this Journal
Abstract
The condensation reaction of (benzylene)triphenylphosphoranes with carbonyl compounds in supercritical carbon dioxide was examined. Reactions of (benzylene)phosphoranes (ca. 1 mmol) with several benzaldehydes in a supercritical carbon dioxide (80 $^{\circ}C$, 2,000 psi) containing THF entrainer (5%) in a 24 mL reactor proceed smoothly to yield olefination products in fairly good to excellant yields but slower, compared to reactions in a conventional THF solvent. Generally, phosphoranes that are not substituted with a nitro group show more (Z)-selective reactions with aromatic aldehydes under $scCO_2$ condition than in THF. The reaction of (benzylene)triphenylphosphoranes with 4-t-butylcyclohexanone gave the corresponding olefin compounds with a low conversion under both the supercritical carbon dioxide and the organic THF solvent. Our preliminary study showed the Wittig reaction carries out smoothly in supercritical carbon dioxide medium and also a possibile tunability of this reaction pathway by adding a entrainer. The results would be useful for devising a novel process for the environmentally friendly Wittig reaction.
Keywords
Supercritical; Carbon dioxide; Phosphoranes; Phosphorus Ylides; Wittig reaction;
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  • Reference
1 Balema, V. P.; Wiench, J. W.; Pruski, M.; Pecharsky, V. K. J. Am. Chem. Soc. 2002, 124, 6244.   DOI   ScienceOn
2 Anastas, P. T.; Williamson, T. C. Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes; Oxford University Press: Oxford, 1988.
3 Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1988.
4 Oakes, R. S.; Clifford, A. A.; Rayner, C. M. J. Chem. Soc. Perkins Trans. 1, 2001, 917.
5 Clifford, A. A. Fundamentals of Supercritical Fluids; Oxford University Press: Oxford, 1998.
6 Brennecke, J. F.; Chateauuneuf, J. E. Chem. Rev. 1999, 99, 433.   DOI   ScienceOn
7 Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065.   DOI   ScienceOn
8 Holmes, J. D.; Bhargava, P. A.; Korgel, B. A.; Johnston, K. P. Langmuir 1999, 15, 6613.   DOI   ScienceOn
9 Maryanoff, B. E.; Reitz, A. B., Chem. Rev. 1989, 89, 863.   DOI
10 Maercker, A. Org. React. 1965, 14, 270.
11 Doobs, J. M.; Wong, J. M.; Lahiere, R. J. Ind. Eng. Chem. Res. 1987, 26, 56.   DOI   ScienceOn
12 Hanessian, S.; Beaudoin, S. Tetrahedron Lett. 1992, 33, 7655.   DOI   ScienceOn
13 Ohde, H.; Ohde, M.; Bailey, M.; Kim, H.; Wai, C. M. Nano Lett. 2002, 2, 721   DOI   ScienceOn
14 Reaves, J. T.; Griffith, A. T.; Roberts, C. A. J. Chem. Eng. Data. 1998, 43, 683.   DOI   ScienceOn
15 Andrus, M. B.; Mendenhall, K. G.; Meredith, E. L.; Sekhar, B. B. V. S. Tetrahedron Lett. 2002, 43, 1789.   DOI   ScienceOn
16 Pommer, H.; Thieme, P. C. Topics Curr. Chem. Chem. 1983, 109, 165.   DOI
17 Eckert, C. A.; Chandler, K. Proc. 4th Int. Symp. on Supercritical Fluids: Sendai, Japan, 1997. pp. 799-806.
18 VanNieuwenhze, M. S.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7864.   DOI   ScienceOn
19 Jessop, P. G.; Hasiao, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 344.   DOI   ScienceOn
20 Tester, J. W.; Danheiser, R. L.; Weinstein, R. D.; Renzo, A.; Taylor, J. D.; Steinfeld, I. J. In ACS Symp. Ser. 767; ACS: Washington D. C., 2000.
21 Johnson, A. W., Ylides and Imines of Phosphorus; John Wiley & Sons: New York, 1993.
22 Mesiano, A. J.; Beckmann, E. J.; Russell, R. A. Chem. Rev. 1999, 99, 623.   DOI   ScienceOn
23 Singh, A. K.; Kanvah, S. J. Chem. Soc. Perkin Trans. II 2001, 3, 395.
24 Huang, Z.-Z.;Ye, S.; Xia, W.; Yu, Y.-H.; Tang. Y. J. Org. Chem. 2002, 67, 3096.   DOI   ScienceOn
25 Eastoe, J.; Cazelles, B. M.; Steytler, D. C.; Holmes, J. D.; Pitt, A. R.; Wear, T. J.; Heenan, R. K. Langmuir 1997, 13, 6980.   DOI   ScienceOn
26 Johnson, A. W.; Kyllingsatd, V. L. J. Org. Chem. 1966, 31, 334.   DOI
27 Anstead, G. M.; Katzenellenbogen, J. A. J. Phys. Chem. 1988, 92, 6249.   DOI
28 Baker, R. T.; Tumas, W. Science 1999, 284, 1477.   DOI   ScienceOn
29 Wittig, G.; Schlosser, M. Tetrahedron 1962, 18, 1023.   DOI   ScienceOn
30 Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron 1998, 54, 15525.   DOI   ScienceOn
31 Marquet, J.; Moreno-Manas, M.; Pacheco, P.; Prat, M.; Katritzky, A. R.; Brycki, B. Tetrahedron 1990, 46, 5333.   DOI   ScienceOn
32 Chemical Synthesis using Supercritical Fluids; Jessop, P. G., Leitner, W., Eds.; Wiley-VCH: Weinheim, 1999.
33 Gillespie, R. J.; White, R. F. M. In Progress in Sterochemistry; Butterworths: London, 1971; Vol. 3.
34 Kuo, E. A.; Hambleton, P. T.; Kay, D. P.; Evans, P. L.; Matharu, S. S. J. Med. Chem. 1996, 39, 4608.   DOI   ScienceOn
35 Jeong, N.; Hwang, S. H. Angew. Chem., Int. Ed. Engl. 2000, 39, 636   DOI   ScienceOn
36 Hadida, S.; Super, M. S.; Beckmann, E. J.; Curran, D. P. J. Am. Chem. Soc. 1997, 119, 7406.   DOI   ScienceOn
37 Wan, P.; Davis, M. J.; Teo, M.-A. J. Org. Chem. 1989, 54, 1354.   DOI
38 Hoffmann, R. W. Angew. Chem. Int. Ed. 2001, 40, 1411.   DOI   ScienceOn
39 Nave, S.; Eastoe, J.; Penfold, J. Langmuir 2000, 16, 8733.   DOI   ScienceOn
40 Wittig, G.; Geissler, G. Liebigs Ann. Chem. 1953, 580, 44.   DOI
41 Johnson, A. W. Ylide Chemistry; Academic Press: New York, 1966.
42 Kolodiazhnyi, O. I., Phosphorus Ylides: Chemistry and Application in Organic Synthesis; Wiley-VCH: New York, 1999.