Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2016, Article ID 3518102, 7 pages
http://dx.doi.org/10.1155/2016/3518102
Research Article

Two New 1,1,3,3-Tetramethylguanidinium Halochromates (C5H14N3CrO3X) (X: Cl, F): Efficient Reagents for Oxidation of Organic Substrates under Solvent-Free Conditions and Microwave Irradiation

1Department of Chemistry, Faculty of Science, Kafkas University, 36100 Kars, Turkey
2Department of Chemistry, Faculty of Science, Gazi University, 06100 Ankara, Turkey

Received 27 January 2016; Revised 27 March 2016; Accepted 11 April 2016

Academic Editor: Cristina Femoni

Copyright © 2016 Kıvılcım Şendıl et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. F. A. Luzzio and F. S. Guziec, “Recent applications of oxochromiumamine complexes as oxidants in organic synthesis. A review,” Organic Preparations and Procedures International, vol. 20, no. 6, pp. 533–584, 1988. View at Publisher · View at Google Scholar
  2. J. C. Collins, W. W. Hess, and F. J. Frank, “Dipyridine-chromium(VI) oxide oxidation of alcohols in dichloromethane,” Tetrahedron Letters, vol. 9, no. 30, pp. 3363–3366, 1968. View at Publisher · View at Google Scholar · View at Scopus
  3. E. J. Corey and J. W. Suggs, “Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds,” Tetrahedron Letters, vol. 16, no. 31, pp. 2647–2650, 1975. View at Publisher · View at Google Scholar · View at Scopus
  4. E. J. Corey and G. Schmidt, “Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media,” Tetrahedron Letters, vol. 20, no. 5, pp. 399–402, 1979. View at Publisher · View at Google Scholar · View at Scopus
  5. M. N. Bhattacharjee, M. K. Chaudhuri, H. S. Dasgupta, N. Roy, and D. T. Khathing, “Pyridinium fluorochromate; a new and efficient oxidant for organic substrates,” Synthesis, vol. 1982, no. 7, pp. 588–590, 1982. View at Publisher · View at Google Scholar
  6. M. N. Bhattcharjee, M. K. Chaudhuri, and S. Purkayastha, “Some aspects of pyridinium fluorochromate, C5H5NHCrO3F (PFC), oxidations. stoichiometry of oxidation of alcohols, evidence for oxygen transfer, and the identity of the reduced chromium species,” Tetrahedron, vol. 43, no. 22, pp. 5389–5392, 1987. View at Publisher · View at Google Scholar
  7. M. K. Chaudhuri, S. K. Chettri, S. Lyndem, P. C. Paul, and P. Srinivas, “Quinolinium fluorochromate (QFC), C9H7NH(CrO3F): an improved Cr(VI)-oxidant for organic substrates,” Bulletin of the Chemical Society of Japan, vol. 67, no. 7, pp. 1894–1898, 1994. View at Publisher · View at Google Scholar
  8. S. Goswami and A. Kar, “Guanidinium chlorochromate, a new, efficient, and mild oxidizing agent for benzylic and other alcohols to carbonyl compounds in water and organic solvents,” Synthetic Communications, vol. 41, no. 17, pp. 2500–2504, 2011. View at Publisher · View at Google Scholar · View at Scopus
  9. R. Srinivasan, C. V. Ramesh, W. Madhulatha, and K. Balasubramanian, “Oxidation of alcohols by quinolinium chlorochromate,” Indian Journal of Chemistry B: Organic Chemistry including Medicinal, vol. 35B, pp. 480–481, 1996. View at Google Scholar
  10. U. Bora, M. K. Chaudhuri, D. Dey, D. Kalita, W. Kharmawphlang, and G. C. Mandal, “3,5-Dimethylpyrazolium fluorochromate(VI), C5H8N2H[CrO3F], (DmpzHFC): a convenient new reagent for oxidation of organic substrates,” Tetrahedron, vol. 57, no. 12, pp. 2445–2448, 2001. View at Publisher · View at Google Scholar · View at Scopus
  11. G. Maier, H. P. Reisenauer, and M. De Marco, “Isonitroso hydrogen (hydroxy nitrene, HON),” Angewandte Chemie—International Edition, vol. 38, no. 1-2, pp. 108–110, 1999. View at Publisher · View at Google Scholar · View at Scopus
  12. A. Bhandari, P. K. Sharma, and K. K. Banerji, “Kinetics and mechanism of the oxidative regeneration of carbonyl compounds from oximes by pyridinium chlorochromate,” Indian Journal of Chemistry—Section A: Inorganic, Physical, Theoretical and Analytical Chemistry, vol. 40, no. 5, pp. 470–474, 2001. View at Google Scholar · View at Scopus
  13. S. Meenakshisundaram and R. Sockalingam, “Kinetics and mechanism of the quinolinium fluorochromate oxidation of some primary, secondary and unsaturated alcohols in acetonitrile,” Collection of Czechoslovak Chemical Communications, vol. 66, no. 6, pp. 877–896, 2001. View at Publisher · View at Google Scholar · View at Scopus
  14. J. H. Clark, S. R. Cullen, S. J. Barlow, and T. W. Bastock, “Environmentally friendly chemistry using supported reagent catalysts—structure-property relationships for clayzic,” Journal of the Chemical Society, Perkin Transactions 2, no. 6, pp. 1117–1130, 1994. View at Google Scholar · View at Scopus
  15. R. S. Varma, R. Dahiya, and R. K. Saini, “Iodobenzene diacetate on alumina: rapid oxidation of alcohols to carbonyl compounds in solventless system using microwaves,” Tetrahedron Letters, vol. 38, no. 40, pp. 7029–7032, 1997. View at Publisher · View at Google Scholar · View at Scopus
  16. J.-D. Lou, L.-H. Zhu, L.-L. Pan, L. Li, F. Li, and C.-L. Gao, “Solventfree oxidation of secondary alcohols with chromium trioxide,” Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, vol. 36, no. 7, pp. 585–587, 2006. View at Publisher · View at Google Scholar · View at Scopus
  17. J.-D. Lou and L.-Z. Wang, “An efficient and selective solvent-free oxidation of alcohols,” Chemical Papers, vol. 57, no. 2, pp. 136–137, 2003. View at Google Scholar · View at Scopus
  18. M. Tajbakhsh, R. Hosseinzadeh, and M. Sadatshahabi, “Synthesis and application of 2,6Dicarboxy pyridinium fluorochromate as a new solidphase oxidant,” Synthetic Communications, vol. 35, no. 11, pp. 1547–1554, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. A. Saffar-Teluri, “Fast selective oxidation of alcohols under solvent-free conditions,” Research on Chemical Intermediates, vol. 39, no. 7, pp. 3337–3343, 2013. View at Publisher · View at Google Scholar · View at Scopus
  20. P. Salehi, H. Firouzabadi, A. Farrokhi, and M. Gholizadeh, “Solvent-free oxidations of alcohols, oximes, aldehydes and cyclic acetals by pyridinium chlorochromate,” Synthesis, no. 15, pp. 2273–2276, 2001. View at Google Scholar · View at Scopus
  21. K. Tanaka and F. Toda, “Solvent-free organic synthesis,” Chemical Reviews, vol. 100, no. 3, pp. 1025–1074, 2000. View at Publisher · View at Google Scholar · View at Scopus
  22. M. M. Kazem, G. Shahriare, and I. Hossein, “Microwave-assisted oxidation of alcohols and polyarenes with cetyltrimethylammonium bromochromate,” Chinese Journal of Chemistry, vol. 27, no. 8, pp. 1501–1504, 2009. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Einhorn, C. Einhorn, F. Ratajczak, and J.-L. Pierre, “Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts,” Journal of Organic Chemistry, vol. 61, no. 21, pp. 7452–7454, 1996. View at Publisher · View at Google Scholar · View at Scopus
  24. L. Ross A and D. S. Donald, “Magtrieve: an efficient, magnetically retrievable and recyclable oxidant,” Tetrahedron Letters, vol. 38, no. 22, pp. 3857–3860, 1997. View at Publisher · View at Google Scholar · View at Scopus
  25. B. Özgün and K. Şendil, “Quinoxalinium Fluorochromate (QxFC): a new and efficient reagent for the oxidation of alcohols in solution, under solvent-free conditions and microwave irradiation,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 181, no. 4, pp. 959–964, 2006. View at Publisher · View at Google Scholar · View at Scopus
  26. B. Özgün, A. Yaylaoglu, and K. Şendil, “4-Benzylpyridinium fluorochromate: an efficient and selective oxidant for organic substrates,” Monatshefte fur Chemie, vol. 138, no. 2, pp. 161–163, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. K. Şendil and B. Özgün, “Dipyrazinium Tri(fluorotrioxochromate): an efficient oxidant for organic substrates,” Monatshefte für Chemie, vol. 137, no. 12, pp. 1529–1533, 2006. View at Publisher · View at Google Scholar · View at Scopus
  28. M. Canbulat and B. Özgün, “3,5-Dimethylpyrazolium chlorochromate(VI): an efficient reagent for solvent-free oxidation of organic substrates,” Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, vol. 42, no. 5, pp. 634–637, 2012. View at Publisher · View at Google Scholar · View at Scopus
  29. Z. Rapport, Handbook of Tables for organic Compounds Identification, CRC Press, Boca Raton, Fla, USA, 3rd edition, 1976.
  30. E. J. Corey and D. L. Boger, “Oxidative cationic cyclization reactions effected by pyridinium chlorochromate,” Tetrahedron Letters, vol. 19, no. 28, pp. 2461–2464, 1978. View at Publisher · View at Google Scholar · View at Scopus
  31. M. K. Chaudhuri, S. K. Dehury, S. S. Dhar, and U. B. Sinha, “The economic synthesis of pyridinium fluorochromate (VI), C5H5NH[CrO3] (PFC), and solvent-free oxidation of organic substrates with PFC,” Synthetic Communications, vol. 34, no. 22, pp. 4077–4087, 2004. View at Publisher · View at Google Scholar
  32. K. Şendil, Synthesis and characterization of some oxochromdichromates, halochromates, investigation of oxidation reactions of various organic compounds in different mediums [Ph.D. thesis], 2005, https://tez.yok.gov.tr/UlusalTezMerkezi/tezSorguSonucYeni.jsp.
  33. A. R. Hajipour, H. R. Bagheri, and A. E. Ruoho, “Solid state oxidation of alcohols using 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate,” Bulletin of the Korean Chemical Society, vol. 25, no. 8, pp. 1238–1240, 2004. View at Publisher · View at Google Scholar · View at Scopus
  34. M. K. Chaudhuri, S. K. Dehury, S. Hussain, A. Duarah, and N. Gogoi, “The selective solid-phase oxidation of alcohols and other organic substrates by 3,5-dimethylpyrazolium Fluorochromate,” Organic Preparations and Procedures International, vol. 38, no. 3, pp. 331–336, 2006. View at Publisher · View at Google Scholar · View at Scopus