Oxidation

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 chromic oxide and potassium permanganate, have been exploited for many years. Especially, chromic oxide has been utilized abundantly, based on the report of the control of oxidization powers by Jones or Sarett.1) Furthermore, chromic oxides have been improved as the Collins reagent2), PCC3) and PDC4) and are used in many fields. On the other hand, Dess-Martin periodinane5) and the Mukaiyama oxidizing agent6) 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.

A2065 A2065 A1348 A1348 B2134 B2134
B2897 B2897 B1375 B1375 B2539 B2539
B1123 B1123 B1616 B1616 T0617 T0617
B2240 B2240 B2188 B2188 C1326 C1326
C1327 C1327 C0076 C0076 T0061 T0061
T0970 T0970 C1944 C1944 D2045 D2045
D3411 D3411 D0318 D0318 D3219 D3219
D3220 D3220 D3428 D3428 D3429 D3429
H0878 H0878 P1015 P1015 I0330 I0330
I0479 I0479 I0073 I0073 L0021 L0021
L0069 L0069 M1774 M1774 M2072 M2072
M1197 M1197 M0981 M0981 M1775 M1775
O0308 O0308 P1910 P1910 P1415 P1415
O0310 O0310 P0557 P0557 P0998 P0998
P0930 P0930 P0931 P0931 P1088 P1088
Q0058 Q0058 S0815 S0815 T0836 T0836
T1803 T1803 T1560 T1560 T1559 T1559
T0466 T0466 T1362 T1362 T1837 T1837
T2507 T2507 T1956 T1956 T2038 T2038
T1957 T1957
A2065 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate
A1348 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical [Catalyst for Oxidation]
B2134 Benzeneseleninic Acid
B2897 9-(2-Biphenylyl)-10-methylacridinium Perchlorate
B1375 Bis(4-methoxyphenyl) Selenoxide
B2539 Bis(pyridine)iodonium Tetrafluoroborate
B1123 Bis(tetrabutylammonium) Dichromate [Oxidizing Reagent]
B1616 [Bis(trifluoroacetoxy)iodo]pentafluorobenzene
T0617 Bromanil
B2240 N-tert-Butylbenzenesulfenamide
B2188 N-tert-Butylbenzenesulfinimidoyl Chloride [Oxidizing Reagent]
C1326 (2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
C1327 (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
C0076 Chloramine T Trihydrate
T0061 Chloranil
T0970 o-Chloranil
C1944 Chloronitrosyl[N,N'-bis(3,5-di-tert-butylsalicylidene)-1,1,2,2-tetramethylethylenediaminato]ruthenium(IV)
D2045 Dess-Martin Periodinane
D3411 Di-tert-butyl Peroxide
D0318 Dichloramine T
D3219 2,6-Dichloropyridine N-Oxide
D3220 4-(Dimethylamino)pyridine N-Oxide Hydrate
D3428 9-(2,5-Dimethylphenyl)-10-methylacridinium Perchlorate
D3429 9-(2,6-Dimethylphenyl)-10-methylacridinium Perchlorate
H0878 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Benzoate Free Radical [Catalyst for Oxidation]
P1015 [Hydroxy(tosyloxy)iodo]benzene
I0330 Iodobenzene Diacetate
I0479 Iodomesitylene Diacetate
I0073 2-Iodosobenzoic Acid
L0021 Lead Tetraacetate (contains Acetic Acid)
L0069 2,6-Lutidine N-Oxide
M1774 9-Mesityl-10-methylacridinium Perchlorate
M2072 9-Mesityl-2,7,10-trimethylacridinium Perchlorate
M1197 4-Methoxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical [Catalyst for Oxidation]
M0981 4-Methylmorpholine N-Oxide (50% in Water, ca. 4.8mol/L)
M1775 10-Methyl-9-phenylacridinium Perchlorate
O0308 Osmium Tetroxide (4% in Water)
P1910 Phosphomolybdic Acid Hydrate
P1415 Poly[4-(diacetoxyiodo)styrene]
O0310 Potassium Peroxymonosulfate [>45%(T) as KHSO5]
P0557 Pyridine N-Oxide
P0998 Pyridine - Sulfur Trioxide Complex
P0930 Pyridinium Chlorochromate
P0931 Pyridinium Dichromate
P1088 Pyridinium Fluorochromate
Q0058 Quinolinium Dichromate
S0815 Silver(II) Pyridine-2-carboxylate
T0836 Tetrabutylammonium Perchlorate
T1803 Tetrabutylammonium Perrhenate
T1560 2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical
T1559 Tetrapropylammonium Perruthenate
T0466 Trimethylamine N-Oxide Dihydrate
T1362 Trimethylamine N-Oxide Anhydrous
T1837 Triphenylbismuth Dichloride
T2507 Triphenyl-2,6-xylylbismuthonium Tetrafluoroborate
T1956 Tris(2-methoxyphenyl)bismuth Dichloride
T2038 Tris(4-trifluoromethylphenyl)bismuth Dichloride
T1957 Tri-o-tolylbismuth Dichloride
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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.

Literature

1) K. Bowden, I. M. Heilbron, E. R. H. Jones, B. C. l. Weedon, J. Chem. Soc., 1946, 39 [DOI]; S. V. Ley, A. Madin, Comprehensive Organic Synthesis, 1991, 7, 253 (Review).
2) J. C. Collins, W. W. Hess, F. J. Frank, Tetrahedron Lett., 1968, 3363 [DOI].
3) E. J. Corey, J. W. Suggs, Tetrahedron Lett., 1975, 2647 [DOI].
4) E. J. Corey, G. Schmidt, Tetrahedron Lett., 1979, 399 [DOI].
5) D. B. Dess, J. C. Martin, J. Org. Chem., 1983, 48, 4155 [DOI]; R. E. Irekand, L. Liu, J. Org .Chem., 1993, 58, 2899 [DOI].
6) J. Matsuo, D. Iida, K. Tatani, T. Mukaiyama, Bull. Chem. Soc. Jpn., 2002, 75, 223 [DOI].
7) W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625 [DOI]; S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis, 1994, 639 (Review) [DOI].
8) O. L. Lebelev, S. N. Kazarnovskii, Zhur. Obshch. Khim., 1960, 30, 1631; A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Synthesis, 1996, 1153 (Review) [DOI].

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