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.

C1326 C1326 C1327 C1327 M1775 M1775
T1560 T1560 D3219 D3219 L0069 L0069
I0073 I0073 C0357 C0357 D3220 D3220
A2065 A2065 A1348 A1348 H0878 H0878
M1197 M1197 M0981 M0981 D3428 D3428
D3429 D3429 B2897 B2897 M1774 M1774
M2072 M2072 B2134 B2134 B1375 B1375
B1123 B1123 B2151 B2151 B3497 B3497
T0617 T0617 C0076 C0076 T0061 T0061
C1944 C1944 D2045 D2045 D3411 D3411
D0318 D0318 I0330 I0330 I0479 I0479
I0072 I0072 L0021 L0021 M0927 M0927
B2240 B2240 B2188 B2188 T0970 T0970
P1415 P1415 P0998 P0998 P0557 P0557
P0930 P0930 P0931 P0931 P1088 P1088
Q0058 Q0058 S0815 S0815 H0362 H0362
T0836 T0836 T1803 T1803 T0839 T0839
T1559 T1559 T1957 T1957 T0466 T0466
T1362 T1362 T2507 T2507 T1837 T1837
T1956 T1956 T2038 T2038 B1175 B1175
B1616 B1616 P1015 P1015
C1326 (2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
C1327 (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
M1775 10-Methyl-9-phenylacridinium Perchlorate
T1560 2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical
D3219 2,6-Dichloropyridine N-Oxide
L0069 2,6-Lutidine N-Oxide
I0073 2-Iodosobenzoic Acid
C0357 3-Chloroperoxybenzoic Acid (contains ca. 30% Water)
D3220 4-(Dimethylamino)pyridine N-Oxide Hydrate
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]
H0878 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Benzoate Free Radical [Catalyst for Oxidation]
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)
D3428 9-(2,5-Dimethylphenyl)-10-methylacridinium Perchlorate
D3429 9-(2,6-Dimethylphenyl)-10-methylacridinium Perchlorate
B2897 9-(2-Biphenylyl)-10-methylacridinium Perchlorate
M1774 9-Mesityl-10-methylacridinium Perchlorate
M2072 9-Mesityl-2,7,10-trimethylacridinium Perchlorate
B2134 Benzeneseleninic Acid
B1375 Bis(4-methoxyphenyl) Selenoxide
B1123 Bis(tetrabutylammonium) Dichromate [Oxidizing Reagent]
B2151 Bis(tetrabutylammonium) Peroxydisulfate
B3497 Bis(trimethylsilyl) Peroxide (contains Hexamethyldisiloxane) (ca. 30% in Hexane)
T0617 Bromanil
C0076 Chloramine T Trihydrate
T0061 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
I0330 Iodobenzene Diacetate
I0479 Iodomesitylene Diacetate
I0072 Iodosobenzene
L0021 Lead Tetraacetate (contains Acetic Acid)
M0927 Monoperoxyphthalic Acid Magnesium Salt Hexahydrate
B2240 N-tert-Butylbenzenesulfenamide
B2188 N-tert-Butylbenzenesulfinimidoyl Chloride [Oxidizing Reagent]
T0970 o-Chloranil
P1415 Poly[4-(diacetoxyiodo)styrene]
P0998 Pyridine - Sulfur Trioxide Complex
P0557 Pyridine N-Oxide
P0930 Pyridinium Chlorochromate
P0931 Pyridinium Dichromate
P1088 Pyridinium Fluorochromate
Q0058 Quinolinium Dichromate
S0815 Silver(II) Picolinate
H0362 tert-Butyl Hypochlorite
T0836 Tetrabutylammonium Perchlorate
T1803 Tetrabutylammonium Perrhenate
T0839 Tetraethylammonium Perchlorate
T1559 Tetrapropylammonium Perruthenate
T1957 Tri-o-tolylbismuth Dichloride
T0466 Trimethylamine N-Oxide Dihydrate
T1362 Trimethylamine N-Oxide Anhydrous
T2507 Triphenyl-2,6-xylylbismuthonium Tetrafluoroborate
T1837 Triphenylbismuth Dichloride
T1956 Tris(2-methoxyphenyl)bismuth Dichloride
T2038 Tris(4-trifluoromethylphenyl)bismuth Dichloride
B1175 [Bis(trifluoroacetoxy)iodo]benzene
B1616 [Bis(trifluoroacetoxy)iodo]pentafluorobenzene
P1015 [Hydroxy(tosyloxy)iodo]benzene
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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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