Two-phase Wittig reaction of synthesizing liquid crystal intermediate by active quaternary phosphonium salt

Chemical Engineering Communications

Volumn 195, Issue 7, 2008, Pages 770-786

  Wang, Maw Ling ^a   Liu, Biing Lang ^b   Lin, Shan Je ^c  

^a HUNGKUANG UNIVERSITY   (Taiwan)

^b WUFENG INSTITUTE OF TECHNOLOGY   (Taiwan)

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Active quaternary phosphonium salt; Methyl 4 4 (nonyloxy) styryl benzoate ; Synthesis and kinetics; Two phase reaction

Indexed keywords

ALDEHYDES; ORGANIC SOLVENTS; REACTION KINETICS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ACTIVE QUATERNARY PHOSPHONIUM SALT; TWO-PHASE REACTION; WITTIG REACTION;

LIQUID CRYSTALS;

ALDEHYDES; LIQUID CRYSTALS; ORGANIC SOLVENTS; REACTION KINETICS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 41049112125     PISSN: 00986445     EISSN: 15635201     Source Type: Journal    
DOI: 10.1080/00986440701690956     Document Type: Article

References (23)

1. Anzalone, L. and Hirsch, J. A. (1985) Substituent effects on hydrogenation of aromatic ring hydrogenation vs. hydrogenolysis in cyclic analogue of benzyl ethers. J. Org. Chem., 50, pp. 2218-2133.
2. Dehmlow, E. V. and Dehmlow, S. S. (1993) Phase Transfer Catalysis,, VCH, New York
3. Freedman, H. H. (1986) Industrial applications of phase-transfer catalysis (PTC): Past, present and future. Pure Appl. Chem., 58, pp. 857-868.
4. Fujiwara, Y., Moritani, I. and Teranishi, S. (1968) Aromatic substitution of olefins. IV: Reaction with palladium metal and silver acetate. Tetrahedron Lett., 35, pp. 3863-3865.
5. Huang, S. T., Kuo, H. S. and Chen, C. T. (2001) Total synthesis of NADH: Ubiquinone oxidoreductase (complex I) antagonist pterulone and its analogue. Tetrahedron Lett., 42, pp. 7473-7475.
6. Johnson, A. W. and Kyllingstad, V. L. (1966) Chemistry of ylids. XII: Effect of phosphorus substituents on the stereochemistry of the Wittig reaction. J. Org. Chem., 31, pp. 334-336.
7. Kaye, I. A. and Chester, L. P. (1953) Use of 2-ammonpyridine in the Voigt reaction. J. Am. Chem. Soc., 75, pp. 746-748.
8. Keller, W. E. (1986) Phase-Transfer Reactions, 1, Georg Thieme Verlag, New York
9. Keller, W. E. (1987) Phase-Transfer Reactions, 2, Georg Thieme Verlag, New York
10. Starks, C. M. (1985) Phase-Transfer Catalysis: New Chemistry, Catalysts, and Applications, pp. 1-7. American Chemical Society, Washington, D.C
11. Starks, C. M., Liotta, C. L. and Halpern, M. E. (1994) Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives, Academic Press, New York
12. Tagaki, W., Inoue, I. and Yano, Y. (1974) Reduction of 2,3,4,5-tetraphenyl cyclopentadiene (tetracyclone). Tetrahedron Lett., 30, pp. 2587-2589.
13. Thomas, G. I., Bohner, C., Ladlow, M. and Spring, D. R. (2005) Synthesis and utilization of functionalized polystyrene resins. Tetrahedron, 61, pp. 12153-12159.
14. Wang, M. L. and Chang, S. W. (1998) Kinetic study of synthesizing unsymmetric acetals under phase transfer conditions. Chem. Eng. Commun., 164, pp. 79-97.
15. Wang, M. L. and Chen, W. H. (2007) Kinetic study of the synthesizing dialkoxymethane using 4-(trialklammonium)propanultans as new phase-transfer catalysts. Chem. Eng. Commun., 194, pp. 19-36.
16. Wang, M. L. and Huang, T. H. (2006) Kinetic study of benzyl alcohol oxidation under phase transfer catalysis conditions. Chem. Eng. Commun., 194, pp. 618-634.
17. Wang, M. L. and Lam, G. K. (2004) Hydrolysis of ethyl-2-bromoisobutyrate in an alkaline solution. Chem. Eng. Commun., 191, pp. 220-340.
18. Wang, M. L., Ou, C. C. and Jwo, J. J. (2000) Study of the reaction of glycine and benzoyl chloride under inverse phase transfer catalysis. Chem. Eng. Commun., 179, pp. 233-252.
19. Wang, M. L., Hsu, S. L. and Hsieh, Y. M. (2006) Synthesis of dialkoxymethane at high alkaline concentration via phase transfer catalysis. Chem. Eng. Commun., 193, pp. 1368-1383.
20. Weber, W. P. and Gokel, G. W. (1977) Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, New York
21. Wittig, G. and Schollkopf, U. (1975) Magnetic resonance studies. I: Investigation of phosphorous compounds by 13 & C and 31P nuclear magnetic resonance for phosphonium salts containing saturated groups. J. Am. Chem. Soc., 97, pp. 2942-2945.
22. Wood, J. H., Bacon, J. A., Meibuhm, A. W. and Turner, G. P. (1941) Preparation of isostilbene. J. Am. Chem. Soc., 63, pp. 1334-1335.
23. Wu, F., Tian, W., Sun, J., Shen, J., Pan, X. and Su, Z. (2001) Study on the electronic structure of phenylene vinylene dimers with different substituents. Mater. Sci. Eng., pp. 165-168.