Pyridinium dichromate acts as a strong oxidizing agent used in the conversion of primary alcohols and secondary alcohols to aldehydes and ketones respectively. It plays an important role in the oxidation of unsaturated tertiary alcohols, silyl ethers, the carbon-boron bond, and oximes. Further, it is used in the conversion of acetals to esters and didehydroketones to enones in the presence of tert-butyl hydroperoxide.
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Applications
Pyridinium dichromate acts as a strong oxidizing agent used in the conversion of primary alcohols and secondary alcohols to aldehydes and ketones respectively. It plays an important role in the oxidation of unsaturated tertiary alcohols, silyl ethers, the carbon-boron bond, and oximes. Further, it is used in the conversion of acetals to esters and didehydroketones to enones in the presence of tert-butyl hydroperoxide.
Solubility
Soluble in water, dimethyl formamide, dimethyl sulfoxide and acetonitrile. Slightly soluble in dichloromethane, chloroform and acetone. Insoluble in hexane, ether and ethyl acetate.
Notes
Hygroscopic. Incompatible withorganic materials and powdered metals.
RUO – Research Use Only
General References:
- Selective oxidant which can be used in dichloromethane to convert primary alcohols to aldehydes: Tetrahedron Lett., 399 (1979). Can also be used catalytically in combination with Sodium percarbonate, A16045, as co-oxidant for conversion of allylic and benzylic alcohols to aldehydes under phase-transfer conditions: Tetrahedron Lett., 35, 1989 (1994). Under the same conditions, ɑ-functionalized benzylic alcohols undergo oxidative cleavage: Synth. Commun., 25, 2051 (1995).
- Matsunaga, K.; Hirajima, H.; Kishida, A.; Takatori, K.; Nagaoka, H. Novel PDC catalyzed oxidative rearrangement of tertiary allylic alcohols to beta-substituted enones. Tetrahedron Lett. 2015, 56 (43), 5941-5944.
- Ghosh, A.; Saha, R.; Mukherjee, K.; Ghosh, S. K.; Sar, P.; Malik, S.; Saha, B. Choice of suitable micellar catalyst for 2,2'-bipyridine-promoted chromic acid oxidation of glycerol to glyceraldehyde in aqueous media at room temperature. Res. Chem. Intermed. 2015, 41 (5), 3057-3078.