Methyltriphenylphosphonium Halochromates, [Me(Ph)3P][CrO3X] (MTriPPXC) (X= F, Cl, Br): the Three New, Mild and Stable Oxidants for Organic Substrates

Methyltriphenylphosphonium Halochromates (MTriPPXC) were prepared and used for oxidation of alcohols under mild conditions. These new compounds are more efficient and have certain advantages over similar oxidizing agents in terms of the amount of oxidants, short reaction times, and high yields. Methyltriphenylphosphonium Halochromates, Me(Ph)3PCrO3X (MTriPPXC) (X= F, Cl, Br) are easily synthesized by the reaction of Methyltriphenylphosphonium with an aqueous solution of CrO3 and HX in a 1:1:2 mole ratio. The reactions were carried out in solution, under mild and acid-free conditions.

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  • Corey, E.J., Suggs, J.W., “Pyridinium
  • Chlorochromate; an Efficient Reagent for Oxidation of Primary and Secondary Alcohols to Carbonyl Compounds”, Tetrahedron Lett., 16(31): 2647-2650 (1975).
  • Maier, G., Reisenauer, H.R., Marco, M.D., “Isonitroso Hydrogen (hydroxy nitrene HON)”, Angew. Chem. Int. Ed. Engl., 38(1-2): 108-110 (1999).
  • Bhandari, A., Sharma, P.K., Banerji, K.K., “Kinetics and Mechanism of the Oxidation of Organic Sulfides by Quinolinium Fluorochromate”, J. Chem. Research, 2001(6): 221-223 (2001).
  • Meenahshisundaram, S., Sockalingam, R.,
  • “Kinetics and Mechanism of the Quinolinium Fluorochromate Oxidation of Some Primary, Secondly and Unsaturated Alchohols in Acetonitrile”, Collect. Czech. Chem. Commun., 66(6): 877-896 (2001).
  • Bahttacharjee, M.N., Chauduri, M.K., Purkayastha, S., “Some Aspects of Pyridinium Fluorochromate, C5H5NHClO3F (PFC), Oxidation, Stoichiometry of Oxidation of Alcohols, Evidence for Oxygen Transfer, and the Identity of the Reduced Chromium Species”, Tetrahedron, 43(22): 5380- 5392 (1987).
  • Corey, E.J., Fleet, G.W.J., “Chromium Trioxide- 3,5-Dimethylpyrazole Complex as a Reagent for Oxidation of Alcohols to Carbonyl Compounds”, Tetrahedron Lett., 14(45): 4499-4501 (1973).
  • Heravi, M.M., Kiakoojori, R., Mirza-Aghayan, M., Tabar-Hydar, K., Bolourchian, M., “3- Carboxypyridinium Chlorochromate on Alumina as a Selective Oxidant for Organic Substrates”, Monatsh. Chem., 130(3): 481-483 (1999).
  • Özgün, B., Yaylaoglu, A., Şendil, K., “4- Benzylpyridinium Fluorochromate: An Efficient and Selective Oxidant for Organic Substrates”, Monatsh. Chem., 138(2): 161-163 (2007).
  • Şendil, K., Özgün, B., “Quinoxalinium Fluorochromate (QxFC): A New and Efficient reagent for Oxidation of Alcohols in Solution, Under Solvent-Free Conditions and Microwave Irradiation”, Phosphorous, Sulfur and Silicon and Related Elements, 181(4): 959-964 (2006).
  • Mahjoub, A.R., Ghammami, S., Kassaee, M.Z, “Tetramethylammonium fluorochromate(VI): A New and Efficient Oxidant for Organic Substrates”, Tetrahedron Lett., 44(24): 4555-4557 (2003). [11] Ghammamy, S., Hashemzadeh, A., “Tripropylammonium Fluorochromate (TriPAFC): A Convenient New Reagent for Oxidation of Organic Substrates”, Bull. Korean Chem. Soc., 25(8): 1277-1279 (2004). [12] Ghammamy, S., Mazareey, M., “Tributylammonium chlorochromate, (C4H9)3NH[CrO3Cl], (TriBACC): A New, Mild and Stable Oxidant for Organic Substrates”, J. Serb. Chem. Soc., 70(5): 687-693 (2005).
Gazi University Journal of Science-Cover
  • Yayın Aralığı: Yılda 4 Sayı
  • Başlangıç: 1988
  • Yayıncı: Gazi Üniversitesi, Fen Bilimleri Enstitüsü