Electrochemical chlorination of some 5-unsaturated steroids

• Smiljka Milisavljevic

  Technical Faculty, Kosovska Mitrovica, Priština

• Rastko Vukicevic

  Department of Chemistry, Faculty of Science, Kragujevac

抄録

Five 5-unsaturated steroids were subjected to constant current electrolysis (50 mA) in a dichloromethane solution of tetraethylammonium chloride in an undivided electrolytic cell at room temperature, using a graphite stick as the anode and a cooper spiral as the cathode. The addition of electrochemically generated elemental chlorine onto the double bond of cholesterol derivatives (5-cholestene, cholesteryl acetate, cholesteryl benzoate and 3-chloro-5-cholstene) gave the corresponding 5?,6? -dichlorosteroids, in good yields (70?73 %). The obtained compounds (5?,6? -dichlorocholestane, 5?,6? -dichlorocholestane-3? -yl acetate, 5?,6? -dichlorocholestane-3? -yl benzoate and 3?, 5?,6? -trichlorocholestane) were characterized by physical and spectral data (IR, 1 H?NMR and 13 C?NMR). However, under the same reaction conditions, cholesterol produced amixture of products from which the expected dichloro derivative (3 ? -hydroxy- 5 ?,6 ? -dichlorocholestane) could not be isolated. This compound was prepared by alkaline hydrolysis of 5?,6?-dichlorocholestan-3? -yl acetate and 5?,6? -dichlorocholestan- 3? -yl benzoate in methanol.

収録刊行物

• Journal of the Serbian Chemical Society

  Journal of the Serbian Chemical Society 69 (11), 941-947, 2004

  National Library of Serbia

キーワード

• General Chemistry

詳細情報

• CRID: 1363107368483541632
• NII論文ID: 30017376548
• DOI: 10.2298/jsc0411941m
• ISSN: 18207421
• ISSN: 03525139
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