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Oxidation [Synthetic Reagents]
Oxidation, making its target substance lose electrons, is one of the most basic reactions in organic chemistry and is exemplified by the combination with oxygen or a dehydrogenation reaction. In particular, it is often used for the transformation of alcohols to the corresponding aldehydes, ketones or carboxylic acids. Heavy metal compounds, such as chromium (VI) oxide and potassium permanganate, have been exploited for many years. Especially, chromium (VI) oxide has been utilized abundantly, based on the report of the control of oxidization powers by Jones or Sarett.1) Furthermore, chromium (VI) oxide have been improved as the Collins reagent2), PCC3) and PDC4) and are used in many fields. On the other hand, the Dess-Martin periodinane5), the Mukaiyama oxidizing agent6) and oxoammonium salts have been developed without containing harmful metals. Moreover, oxidation reactions employing inexpensive sodium hypochlorite or molecular oxygen have also been reported in the presence of oxidation catalysts such as tetrapropylammonium perruthenate (TPAP)7) and TEMPO8). This section shows the typical oxidizers and the catalysts used for oxidation reactions.
Many oxidizing agents may cause combustion or explosion upon mixture with flammable materials or upon exposure to heat, shock, and friction etc. Sufficient safety measures, such as using safety shields, wearing protective equipment, and using extreme caution should be taken when working with these reagents as well as disposing of the reagents.
- 1) a) K. Bowden, I. M. Heilbron, E. R. H. Jones, B. C. L. Weedon, J. Chem. Soc. 1946, 39.
- b) Review: S. V. Ley, A. Madin, Comprehensive Organic Synthesis 1991, 7, 253.
- 2) J. C. Collins, W. W. Hess, F. J. Frank, Tetrahedron Lett. 1968, 9, 3363 .
- 3) E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 16, 2647.
- 4) E. J. Corey, G. Schmidt, Tetrahedron Lett. 1979, 20, 399.
- 5) a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
- 6) J. Matsuo, D. Iida, K. Tatani, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2002, 75, 223.
- 7) Review: J. M. Bobbitt, TCIMAIL 2010, number 146, 2. [PDF]
- 8) a) W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc., Chem. Commun. 1987, 1625
- 9) a) O. L. Lebelev, S. N. Kazarnovskii, Zhur. Obshch. Khim. 1960, 30, 1631.