Cycloalkylation reactions of fatty amines with α,ω-dihaloalkanes: Role of bis-quaternary ammonium salts as phase-transfer catalysts

Catalysis Communications

Volumn 8, Issue 6, 2007, Pages 855-860

  Ali, Hanan El Sharkawy ^a  

^a EGYPTIAN PETROLEUM RESEARCH INSTITUTE   (Egypt)

Author keywords

Analytical applications; Bis quaternary amines; Catalyst activity; Cycloalkylation; Liquid liquid reactions; Micellar phase transfer catalysis; Phase transfer catalysis

Indexed keywords

ALKYLATION; CATALYST ACTIVITY; MICELLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITIONS; SURFACE ACTIVE AGENTS;

ANALYTICAL APPLICATIONS; BIS-QUATERNARY AMINES; CYCLOALKYLATION; LIQUID LIQUID REACTIONS; MICELLAR PHASE TRANSFER CATALYSIS; PHASE TRANSFER CATALYSIS;

AMINES;

EID: 34047245828     PISSN: 15667367     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.catcom.2006.09.013     Document Type: Article

References (34)

1. Teoh S.-G., Ang S.-H., Fun H.-K., and Ong C.-W. Synthesis, crystal structure and biological activity of thiophene-2-carboxaldehyde thiosemicarbazone and its tin complex. J. Organomet. Chem. 580 (1999) 17-21
2. Fiamegos Y.C., and Stalikas C.D. Phase-transfer catalysis in analytical chemistry. Anal. Chim. Acta. 550 (2005) 1-12
3. Jin G., Ido T., and Goto S. Rate enhancement effect of third liquid phase on dibenzyl ether production in solid-liquid-liquid phase transfer catalytic system. Catal. Today 79-80 (2003) 471-478
4. Siva A., and Murugan E. Synthesis and characterization of novel multi-site phase transfer catalyst and its catalytic efficiency for dichlorocarbene addition to citral. J. Mol. Catal. A-Chem. 241 (2005) 101-110
5. Makosza M. Pure Appl. Chem. 43 (1975) 439
6. Yang H.-M., and Wu C.-M. Phase-transfer catalyzed allylation of sodium phenoxide in solid-liquid system. J. Mol. Catal. A-Chem. 153 (2000) 83-91
7. Sharma P., Kumar A., and Sharma M. Synthesis of 4-[2-(2-methylprop-1-enylidene)-2,3-dihydro 1Hbenzimidazole-1-yl]-1-napthol via azo group insertion of dimethylvinylidenecarbene under phase transfers catalysis conditions. Catal. Commun. 7 (2005) 18-24
8. Qiu L.-G., Xie A.-J., and Shen Y.-H. Micellar effect of a triazole-based cationic Gemini surfactant on the rate of a nucleophilic aromatic substitution reaction. Colloid Polym. Sci. (2005)
9. Gytis Kazimieras Kupetis, Gintautas Saduikis,Ona Nivinskiene, Olegas Eicher-Lorka, Bis(4-dialkylaminopyridinium-1-yl)alkylene halides as phase-transfer catalysts in the reactions of dichlorocarbene, ISSN0235-7216. Chemija, T. 12 (2001) 4.
10. Idoux J.P., Wysocki R., Young S., Turcot J., Ohlman C., and Leonard R. Synth. Commun. 13 (1983) 139
11. Balakrishnan T., and Jeyachandran J.P. J. Chem. Soc. Perkin Trans. 2 (1995) 2081
12. Wang M., and Hsieh Y.M. J. Mol. Catal. 210 (2004) 59
13. Yadav G.D., and Desai N.M. Phase transfer catalysed alkylation of 2'-hydroxy acetophenone with 1-bromopentane: kinetics and mechanism of liquid-liquid reaction. J. Mol. Catal. A-Chem. 243 (2006) 278-285
14. Mijin D.Z., Jankovic V.D., and Petrovic S.D. Alkylation of N-substituted 2-phenylacetamides. J. Serb. Chem. Soc. 69 2 (2004) 85-92
15. Benaglia M., Cinquini M., Cozzi F., and Tocco G. Tetrahedron Lett. 43 (2002) 3391
16. Jew S., Jeong B., Yoo M., Huh H., and Park H. Chem. Commun. 14 (2001) 1244
17. Park H., Jeong B., Yoo M., Lee J., Park M., Lee Y., Kim M., and Jew S. Angew. Chem., Int. Ed. 41 (2002) 3036
18. Chinchilla R., Mazon P., and Najera C. Tetrahedron-Asymmetr. 13 (2002) 927
19. Park H., Jeong B.S., Yoo M.S., Lee J.H., Park B.S., Kim M.G., and Jew S.S. Tetrahedron Lett. 44 (2003) 3497
20. Jayachandran J.P., Wheeler C., Eason B.C., Eason, Liotta C.L., and Eckert C.A. Phase transfer catalyzed intramolecular cycloalkylation of phenylacetonitrile with α,ω-dibromoalkanes in supercritical ethane. J. Supercrit. Fluid 27 (2003) 179-186
21. Basu Baul T.S., Mizar A., Lyčka A., Rivarola E., Jirásko R., Holčapek M., Vos D.d., and Englert U. Diphenyltin(IV) complexes of the 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-olates: synthesis and multinuclear NMR, 119Sn Mössbauer, electrospray ionization MS, X-ray characterization and assessment of in vitro cytotoxicity. J. Organomet. Chem. 691 (2006) 3416-3425
22. Muller T.E., and Beller M. Chem. Rev. 98 (1998) 675
23. Hickinbottom W.J. J. Chem. Soc. 27 (1930) 992
24. Caspe S. J. Am. Chem. Soc. 54 (1932) 4457
25. Depreux P., Aichaoui H., and Lesienr I. Heterocycles (1993) 1051
26. Gupta P.P., and Sharma J.N. J. Med. Chem. 16 (1973) 797
27. Salvatore R.N., Nagle A.S., Schmidt S.E., and Jung K.W. Org. Lett. 12 (1999) 1893
28. Makosza M., and Jonczyk A. Phase-transfer alkylation of nitriles. Org. Synth. coll. 6 (1988) 897
29. Makosza M., and Jonczyk A. Phase-transfer alkylation of nitriles. Org. Synth. coll. 55 (1976) 91
30. Wang M.-L., and Hsuan Y. Phase transfer catalytic reaction of n-bromobutane and sodium sulfide in a two-phase solution and its kinetics. J. Mol. Catal. A-Chem. 203 (2003) 79-93
31. Sharma P., Kumar A., and Sharma M. Synthesis of 4-[2-(2-methylprop-1-enylidene)-2,3-dihydro-1Hbenzimidazole-1-yl]-1-napthol via azo group insertion of dimethylvinylidenecarbene under phase transfers catalysis conditions. Catal. Commun. 7 (2005) 18-24
32. Safa K.D., and Babazadeh M. Synthesis and reaction of p-vinylbenzyltris(trimethylsilyl)methane. J. Organomet. Chem. 690 (2005) 79-83
33. BoJonsson, Lindman B., Holmbeug K., and Kronberg B. Surfactants and Polymers in Aqueous Solution (1998), John Wiley & Sons pp. 33-59
34. Seo H.S., and McCray J.E. Interfacial tension of chlorinated aliphatic DNAPL mixtures as a function of organic phase composition. Environ. Sci. Technol. 36 (2002) 1292-1298