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Oxidation Brochure CHROM
Oxidation Brochure CHROM
Chromium(VI) compounds are widely used and very powerful oxidation agents1 for several
functional groups.
Their most common application is
the selective oxidation of primary
and secondary alcohols to
aldehydes, ketones,2,3 or carboxylic
acids. Aldehydes derived from
primary alcohols can only be
isolated under certain reaction
conditions or by using specialized
oxidation reagents.
The mechanism of this reaction is known to proceed via chromyl-esters4 which are cleaved to their
products through base-catalysis.
During reaction chromium species of lower oxidation states (IV and V) are also involved5,6.
In aqueous solutions primary alcohols are usually oxidized to carboxylic acids7,8, while in the
absence of water the oxidation will stop at the aldehyde. The complete oxidation to the carboxylic
acid can also be avoided if the intermediately-formed aldehyde are removed from the reaction
mixture by distillation or other means7.
Common reagents for the selective
oxidation of alcohols to aldehydes
and ketones are pyridinium
chlorochromate, known as Corey’s
reagent9, and a mixture of
chromium(VI) oxide and pyridine10,11
in dichloromethane, known as
Collins reagent12.
Acros Organics offers a complete range of chromium based oxidation reagents, presented on the
following pages with additional information and literature.
AMMONIUM DICHROMATE, 99% (20881) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8
BENZYLTRIETHYLAMMONIUM CHLOROCHROMATE, 98% (32760) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
2,2’-BIPYRIDINIUM CHLOROCHROMATE, 97% (21727) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
CHROMIUM(VI) OXIDE, 99.9% (21410) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
CHROMIUM(VI) OXIDE, 99+% (19661) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
CHROMOSULFURIC ACID (29551) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
CHROMYL CHLORIDE, 99+% (19046) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
IMIDAZOLIUM DICHROMATE, 98% (32762) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
POLY (4-VINYLPYRIDINIUM DICHROMATE), CROSS LINKED WITH 2% DVB; 2.2MMOL Cr/G RESIN (21782) 6
POTASSIUM CHLOROCHROMATE, 98% (32761) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
POTASSIUM CHROMATE, P.A. (20234) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . -
POTASSIUM DICHROMATE, 4WT% SOLUTION IN WATER (38280) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
POTASSIUM DICHROMATE, 99.5% (19776) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
POTASSIUM DICHROMATE, P.A. (19659) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
POTASSIUM DICHROMATE, REAGENT ACS (CRYSTALS) (42411) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
PYRIDINIUM CHLOROCHROMATE, 98% (18367) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
PYRIDINIUM DICHROMATE, 98% (20088) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
PYRIDINIUM FLUOROCHROMATE (30248) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
SILICAGEL, FUNCTIONALIZED WITH 20% PYRIDINIUM DICHROMATE (37222) . . . . . . . . . . . . . . . . . . . . 6
SILICAGEL, FUNCTIONALIZED WITH PYRIDINIUM CHLOROCHROMATE (37124) . . . . . . . . . . . . . . . . . . . . 5
SILVER CHROMATE, 99% (21125) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . -
SODIUM DICHROMATE DIHYDRATE, 99% (21924) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
26 F.A.Luzzio, W.J.Moore, J.Org.Chem 58 (1993) 512. 31 C.Limberg, R.Koppe, Inorg.Chem. 38 (1999) 2106.
27 A.L.Etard, Compt. Rend. 90, 534 (1880). 32 K.B. Sharpless and A.Y. Teranishi, J.Org.Chem. 38, 185 (1973).
28 W. H.Hartford, M.Darrin, Chem,Rev. 58, (1958) 1-61. 33 J.-E. Bäckvall, M.W.Young, K.B.Sharpless, Tetrahedron Lett. (1977) 3523 ; K.B. Sharpless, A.Y.
29 M.Torrent, L.Deng, T.Ziegler, Inorg. Chem. 37 (1998) 1307 ; M.Torrent, L.Deng, M.Duran, M. Teranishi, and J.-E. Bäckvall, J. Am. Chem. Soc., 99 (1977) 3120.
Solà, T.Ziegler Can.J.Chem 77 (1999) 1476. 34 F.Freeman, P.J.Cameron, J.Org.Chem. 33 (1968) 3970; F.Freeman, R.H.DuBois, N.J. Yamachika
30 N.Miyaura, J.K.Kochi, J.Am.Chem.Soc.105 (1983) 2368 ; F.W.Bachelor, U.O. Cheriyan, Tetrahedron 25 (1969) 3441, .Freeman, N.J. Yamachika J.Am.Chem.Soc. 94 (1972) 1214.
Can.J.Chem. 54 (1976) 3383 ; F.W.Bachelor, U.O. Cheriyan J.Chem.Soc.Chem.Comm. (1973) 35 K.B.Sharpless, K.Akashi, J.Am.Chem.Soc. 97 (1975) 5927.
195. 36 I.Mohammadpoor.Baltork, M.M. Sadeghi, A.-H. Adibi, Molecules 6 (2001) 900.
3
IMIDAZOLIUM DICHROMATE, 98% (32762)
A selective and mild reagent for the selective
oxidation of allylic and benzylic alcohols to
carbonyl compounds37.
Oximes, hydrazones and semicarbazones are
converted to the corresponding carbonyl
compounds using imidazolium dichromate
adsorbed on alumina38.
40 R.A.Fernandez, Synlett 5 (2003) 741. 42 F.Bonadies, R.DiFabio, C. Bonini, J.Org.Chem. 49 (1984) 1647.
41 E.J.Parish, S.Chitrakorn, Synth.Comm. 15 (1985) 393. 43 Y.-S. Cheng, W.-L. Liu, S.-H. Chen, Synthesis (1980) 223.
5
PYRIDINIUM DICHROMATE, 98% (20088)
SILICAGEL, FUNCTIONALIZED WITH 20% PYRIDINIUM DICHROMATE (37222)
POLY (4-VINYLPYRIDINIUM DICHROMATE), CROSS LINKED WITH 2% DVB;
2.2MMOL Cr/G RESIN (21782)
Pyridinium dichromate, or the Corey Schmitt44 reagent, is a stable orange solid used for the
selective oxidation of allylic alcohols to α,β-unsaturated aldehydes in the presence of other
primary or secondary alcohols.
Depending on the solvent, the reagent oxidizes non-allylic
primary alcohols to the aldehydes in dichloromethaneor to
the carboxylic acidsin dimethylformamide
Another application of PDC is in the aromatization of 1,4-
dihydropyridines45.