International Journal of Applied Science and Engineering
Published by Chaoyang University of Technology

Yi-Ling Liou and Chin-Teh Huang *

Department of Applied Chemistry,Chaoyang University of Technology, Wufong, Taichung 41349, Taiwan, R.O.C.


 

Download Citation: |
Download PDF


ABSTRACT


Various chain-lengths of ω-bromoalkyl carboxylic acids were synthesized from cyclicketones of different ring size via the oxidation to ω-hydroxyalkyl carboxylic acids followedby bromine substitution of hydroxyl group. The oxidation was conducted in acidic condition orin alkaline condition followed by treatment with hydrobromic acid to achieve the bromine substitution.


Keywords: cyclic ketones, hydroxyalkanoic acids, bromoalkanoic acids, hydrogen peroxide, and anti-SARS disinfectant.


Share this article with your colleagues

 


REFERENCES


[1] Sankaranarayanan, S. and Chattopadhyay,S. 1998. Asymmetric synthesisof a cytotoxic amide of Telesto riiseiTetrahedron Asymmetry, 9: 1345-1350.

[2] Plesnicar, B. 1978. “In Trahanovskyoxidation in organic chemistry”, AcademicPress, New York, Part C:254-267.

[3] Sager, W. F. and Duckworth, A. 1955.Oxidative ring enlargement of cyclicketones by peroxytrifluoroacetic acid.Journal of the American Chemical Society,77: 188-190.

[4] Koch, S. S. C. and Chamberlin, A. R.1989. Modified conditions for efficientBaeyer-Villiger oxidation withm-chloroperoxybenzoic acid. SyntheticCommunications, 19: 829-833.

[5] Neimann, K. and Neumann, R. 2000.Electrophilic Activation of HydrogenPeroxide: Selective Oxidation Reactionsin Perfluorinated Alcohol Solvents. OrganicLetters, 2: 2861-2863.

[6] Matsubara, S., Takai, K., and Nozaki, H.1983. Baeyer-Villiger oxidation withbis(trimethylsilyl) peroxide(Me3SiOOSiMe3) under assistance oftin(IV) chloride or boron fluoride-ethylether complex (BF3.OEt2). BulletinChemical Society Japanese, 56:2029-2032.

[7] Yan, Y. Y., Dong, L. M., Guo, J. P.,Huang, M. Y., and Jiang, Y. Y. 1997.Magnesium oxide-supported polytitanazanecopper(II) complex catalyzedaerobic Baeyer-Villiger oxidation of ketonesand cyclohexanol in the presenceof benzaldehyde. Journal of MacromolecularScience, 34: 1097-1104.

[8] Hao, X., Yamazaki, O., Yoshida, A., andNishikido, J. 2003. GreenBaeyer-Villiger oxidation with hydrogenperoxide: Sn[N(SO2C8F17) 2] 4 as ahighly selective Lewis acid catalyst in afluorous biphase system. Green Chemistry,5: 524-528.

[9] Aleman, C., Casanovas, J., Zanuy, D.,and Hall, H. K. Jr. 2005. Systematicevaluation of the conformational propertiesof alphaticω-hydroxy acids. Journalof Organic Chemistry, 70: 2950-2956.

[10] Olah, G. A., Narang, S. C., and Mehrotra,A. K. 1982. Synthetic methods and reactions;Cleavage of ethanediyl S,S-acetals with iodo (bromo) trimethylsilane/dimethyl sulfoxide. Synthesis, 11:965-966.

[11] Kanemitsu, T., Wong, C. H., and Kanie,O. 2002. Solid-Phase Synthesis of Oligosaccharidesand On-Resin QuantitativeMonitoring Using Gated Decoupling13C NMR. Journal of the AmericanChemical Society, 124: 3591-3599.

[12] Zinkevich, E. P., Treboganov, A. D.,Genokhova, N. S., Sarycheva, I. K., andPreobrazhenskii, N. A. 1966. Macrocycliccompounds. VII. Synthesis ofcyclopentadecanone(exaltone) and pentadecanolide(tibetolide). Zhurnal OrganicheskoiKhimii, 2: 2028-2031.

[13] Solladie, G., Rubio, A., Carreno, M. C.,and Garcia Ruano, J. L.1990. Asymmetricsynthesis of orsellinic acid typemacrolides: The example of lasiodiplodin.Tetrahedron. Asymmetry, 3:187-198.

[14] W Kenneth, B. and Roy, F. W. 1991.Lactones 2. Enthalpies of hydrolysis,reduction, and formation of the C4-C13monocyclic lactones. Strain energies andconformations. Journal of the AmericanChemical Society, 113: 7697-7705.

[15] Ruholl, H. and Schaefer, H. J. 1988.Oxidative cleavage of vicinal diols at thenickel hydroxide electrode. Synthesis, 1:54-56.

[16] Habib, R. M., Chiang, C. Y, and Bailey,P. S. 1984. Dicarboxylic acids fromozonnalysis of cycloalkenes. Journal ofOrganic Chemistry, 49: 2780-2784.

[17] Rao, A. V. R., Krishnappa, S., Reddy, K.L. Narasimha, Reddy, K. Ashok, Reddy,and Pulla, S. 1986. Strategy and constructionof macrocyclic compounds.VII. Synthesis of the backbone bistetrahydrofuransystem for synthesis ofrollinicin. Synthetic Communications, 16:1141-1148.

[18] Pawar, D. M., Moody, E. M., and Noe, E.A. 1999. Conformational Study of Oxacyclooctan-2-one by Dynamic NMRSpectroscopy and Computational Methods.Journal of Organic Chemistry, 64:4586-4589.

[19] Ames, D. E., and Islip, P. J. 1961. Synthesesof long-chain acids. II. Synthesisof linoleic acid. Journal Chemical Society,4409-4412.


ARTICLE INFORMATION




Accepted: 2006-12-09
Available Online: 2006-12-01


Cite this article:

Liou, Y.-L., Huang, C.-T. 2006. Investigation on oxidation of cyclic ketones and synthesisof ω-bromoalkanoic acids. International Journal of Applied Science and Engineering, 4, 235–241. https://doi.org/10.6703/IJASE.2006.4(3).235