Unusual electrochemical oxidation of cholesterol.
It has been found that cholesterol undergoes direct electrochemical oxidation on platinum electrode in dichloromethane. Voltammetric measurements show that the process is controlled by the rate of electron transfer and the height of the oxidation peak is linear vs. concentration of cholesterol. Preparative electrolysis with separated cathodic and anodic compartments afforded dicholesteryl ether in a relatively high material yield. Depending on electrolysis conditions (composition of supporting electrolyte and electrolytic cell construction) various by-products with a 3beta-chloro, 3beta-acetoxy, or 3beta-acetylamino group were obtained.
Kowalski
Jan
J
Faculty of Chemistry, Rzeszów University of Technology, PO Box 85, 35-959 Rzeszów, Poland.
Lotowski
Zenon
Z
Morzycki
Jacek W
JW
Płoszyńska
Jolanta
J
Sobkowiak
Andrzej
A
Wilczewska
Agnieszka Z
AZ
D002784:Cholesterol / Q000737:chemistry*; D004563:Electrochemistry; D004572:Electrolysis; D008752:Methylene Chloride / Q000737:chemistry; D010084:Oxidation-Reduction
D008752:Methylene Chloride; D002784:Cholesterol