By Alan H. Haines
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Extra resources for Methods for Oxidation of Organic Compounds. Alcohols, Alcohol Derivatives, Alky Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds Hydroxyarenes and Aminoarenes
Sample text
1 [35-37]. R. M. Evans, Q. Rev. Chem. Soc. 13, 61 (1959). S. P. Korshunov and L. I. Vereshchagin, Russ. Chem. Rev. 35, 942 (1966). 1 [35]. H. Firouzabadi and E . Ghaderi, Tetrahedron Lett. 839 (1978). 1 Permanganate Ion The use of permanganate ion for the conversion of primary alcohols to aldehydes is of synthetic importance only if the product is relatively stable towards the oxidant. 8, entry 1). The oxidation of secondary alcohols having moderate solubility in water is readily achieved in reasonable yield with aqueous potassium permanganate.
It is noteworthy 26 2. O X I D A T I O N O F A L C O H O L S that the oxidation of benzyl alcohol by ί-butyl chromate in benzene is accelerated in the presence of pyridine [5], Oxidation of octa-3,5-dien-2,7-diol to the corresponding dione is successfully achieved, albeit in low yield, with r-butyl chromate in benzene [3] (entry 3), whereas several other oxidants prove unsuccessful for this purpose. The reagent in carbon tetrachloride-pyridine ( 1 : 1 v/v) has been examined as an oxidant for sterols; secondary steroidal alcohols give the corresponding ketones in good yields, but cholesterol undergoes further oxidation to afford cholest-4-ene-3,6-dione [8] (entry 4).
Little, Tetrahedron Lett. 3749 (1977). D . M. A d a m s and J. B . Raynor, / . Chem. Educ. 4 3 , 94 (1966). D . F. Evans, J. Chem. Soc. 4013 (1957). 5. Pyridinium Dichromate * Tetra-n-butylammonium Dichromate, * Tetra-n-butylammonium Hydrogen Chromate, Pyridinium Chlorochromate and Other Lipophilic Salts of Chromic Acid and Dichromic Acid Metal salts of chromic and dichromic acid have poor solubility in most organic solvents, but the corresponding pyridinium and tetraalkylammonium salts often show enhanced solubility in some of the more polar organic solvents, such as dichloromethane, chloroform or 7V,N-dimethylformamide.