Microwave-Assisted Oxidation of Organic Compounds with Cetyltrimethylammonium Chlorochromate

Mohammd Kazem Mohammadi

Faculty of Science, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran.

DOI: 10.4236/ojsta.2013.23011                

Abstract

An efficient and mild methodology for oxidation of organic compounds is described using Cetyltrimethylammonium Chlorochromate (CTMACC) under microwave irradiation. The reactions are performed cleanly and are controlled to stop at aldehyde stage, without over-oxidation and side products. Oxidation of organic compounds to their corresponding carbonyl compouds, are studied under microwave radiation. The easy procedure, simple workup, short reaction times, and excellent yields, are another advantages of this reagent.

Keywords

Oxidation; Organic Compounds; Chlorochromate; Microwave Irradiation

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	B. M. Trost, “Comprehensive Organic Synthesis,” Pergamon Press, New York, 1991.
[2]	M. Hudlicky, “Oxidations in Organic Chemistry,” American Chemical Society, Washington DC, 1990.
[3]	K. Sato, M. Aoki and R. Noyori, “A ‘Green’ Route to Adipic Acid: Direct Oxidation of Cyclohexenes with 30 Percent Hydrogen Peroxide,” Science, Vol. 281, No. 5383, 1998, pp. 1646-1647. doi:10.1126/science.281.5383.1646
[4]	K. Sato, M. Aoki, J. Tagaki and R. Noyori, “Organic Solventand Halide-Free Oxidation of Alcohols with Aqueous Hydrogen Peroxide,” Journal of the American Chemical Society, Vol. 119, No. 50, 1997, pp. 12386-12387. doi:10.1021/ja973412p
[5]	R. S. Varma and R. K. Saini, “Wet Alumina Supported Chromium(VI) Oxide: Selective Oxidation of Alcohols in Solventless System,” Tetrahedron Letters, Vol. 39, No. 12, 1998, pp. 1481-1482. doi:10.1016/S0040-4039(98)00010-0
[6]	S. Patel and B. K. Mishra, “Chromium(VI) Oxidants Having Quaternary Ammonium Ions: Studies on Synthetic Applications and Oxidation Kinetics,” Tetrahedron, Vol. 63, No. 21, 2007, pp . 4367-4406.
[7]	R. S. Varma and R. Dahiya, “Copper(II) Nitrate on Clay (Claycop)-Hydrogen Peroxide: Selective and SolventFree Oxidations Using Microwaves,” Tetrahedron Letters, Vol. 39, No. 11, 1998, pp. 1307-1308. doi:10.1016/S0040-4039(97)10763-8
[8]	R. S. Varma, R. K. Saini and R. Dahiya, “Active Manganese Dioxide on Silica: Oxidation of Alcohols under Solvent-Free Conditions Using Microwaves,” Tetrahedron Letters, Vol. 38, No. 45, 1997, pp. 7823-7824. doi:10.1016/S0040-4039(97)10093-4
[9]	R. A. Abramovitch, “Applications of Microwave Energy in Organic Chemistry. A Review,” Organic Preparations and Procedures International, Vol. 23, No. 6, 1991, pp. 683-711. doi:10.1080/00304949109458244
[10]	J. Azizian, M. K. Mohammadi, O. R. Firuzi, B. Mirza and R. Miri, “Microwave-Assisted Solvent-Free Synthesis of Bis(dihydropyrimidinone)benzenes and Evaluation of their Cytotoxic Activity,” Chemical Biology & Drug Design, Vol. 75, No. 4, 2010, pp. 375-380.
[11]	S. Caddick, “Microwave Assisted Organic Reactions,” Tetrahedron, Vol. 51, No. 38, 1995, pp. 10403-10432. doi:10.1016/0040-4020(95)00662-R
[12]	C. R. Strauss and R. W. Trainor, “Developments in Microwave-Assisted Organic Chemistry,” Australian Journal of Chemistry, Vol. 48, No. 10, 1995, pp. 1665-1692. doi:10.1071/CH9951665
[13]	D. Bogdal and M. Warzala, “Microwave-Assisted Preparation of Benzo[b]furans under Solventless Phase-Transfer Catalytic Conditions,” Tetrahedron, Vol. 56, No. 44, 2000, pp. 8769-8773. doi:10.1016/S0040-4020(00)00818-8
[14]	J. A. Seijas, M. P. Vazquez-Tato and J. Crecente-Campo, “Straightforward Microwave-Assisted Synthesis of 2Thiazolines Using Lawesson’s Reagent under SolventFree Conditions,” Tetrahedron, Vol. 64, No. 39, 2008, pp. 9280-9285.
[15]	D. Bogdal, J. Pielichowski and K. Jaskot, “A Rapid Williamson Synthesis under Microwave Irradiation in Dry Medium,” Organic Preparations and Procedures International, Vol. 30, No. 4, 1998, pp. 427-432. doi:10.1080/00304949809355304
[16]	R. S. Varma and R. Dahiya, “The Design and Synthesis of a Conformationally Constrained Trisaccharide for Probing Carbohydrate-Protein Interactions,” Tetrahedron Letters, Vol. 38, No. 11, 1997, pp. 2023-2026. doi:10.1016/S0040-4039(97)00223-2
[17]	R. S. Varma, R. K. Saini and H. M. Meshram, “Selective Oxidation of Sulfides to Sulfoxides and Sulfones by Microwave Thermolysis on Wet Silica-Supported Sodium Periodate,” Tetrahedron Letters, Vol. 38, No. 37, 1997, pp. 6525-6528. doi:10.1016/S0040-4039(97)01520-7
[18]	R. S. Varma and R. K. Saini, “Wet Alumina Supported Chromium(VI) Oxide: Selective Oxidation of Alcohols in Solventless System,” Tetrahedron Letters, Vol. 39, No. 12, 1998, pp. 1481-1482. doi:10.1016/S0040-4039(98)00010-0
[19]	R. S. Varma, K. S. Saini and R. Dahiya, “Active Manganese Dioxide on Silica: Oxidation of Alcohols under Solvent-Free Conditions Using Microwaves,” Tetrahedron Letters, Vol. 38, No. 45, 1997, pp. 7823-7824. doi:10.1016/S0040-4039(97)10093-4
[20]	R. S. Varma, R. K. Saini and H. M. Meshram, “Selective Oxidation of Sulfides to Sulfoxides and Sulfones by Microwave Thermolysis on Wet Silica-Supported Sodium Periodate,” Tetrahedron Letters, Vol. 38, No. 37, 1997, pp. 6525-6528.
[21]	K. Bougrin, A. Loupy and M. Soufiaoui, “MicrowaveAssisted Solvent-Free Heterocyclic Synthesis,” Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 6, No. 2-3, 2005, pp. 139-167.
[22]	L. Palombi, F. Bonadies and A. Scettri, “MicrowaveAssisted Oxidation of Saturated and Unsaturated Alcohols with T-Butyl Hydroperoxide and Zeolites,” Tetrahedron, Vol. 53, No. 46, 1997, pp. 15867-15876. doi:10.1016/S0040-4020(97)10047-3
[23]	A. R. Mahjoub, S. Ghammami and M. Z. Kassaee, “Tetramethylammonium Fluorochromate(VI): A New and Efficient Oxidant for Organic Substrates,” Tetrahedron Letters, Vol. 44, No. 24, 2003, pp. 4555-4557. doi:10.1016/S0040-4039(03)00989-4
[24]	M. N. Bhattacharjee, M. K. Chaudhuri, H. S. Dasgupta and N. Roy, “Pyridinium Fluorochromate; A New and Efficient Oxidant for Organic Substrates,” Synthesis, Vol. 1982, No. 7, 1982, pp. 588-590. doi:10.1055/s-1982-29872
[25]	G. Piancatelli, A. Scettri and M. D. Auria, “Pyridinium Chlorochromate: A Versatile Oxidant in Organic Synthesis,” Synthesis, Vol. 1982, No. 4, 1982, pp. 245-258. doi:10.1055/s-1982-29766