Electrochemical chlorination of some 5-unsaturated steroids
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 electrochemi...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Serbian Chemical Society
2004-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2004/0352-51390411941M.pdf |
| Summary: | 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 5α,6β -dichlorosteroids, in good yields (70–73 %). The obtained compounds (5α,6β -dichlorocholestane, 5α,6β -dichlorocholestane-3β -yl acetate, 5α,6β -dichlorocholestane-3β -yl benzoate and 3β, 5α,6β -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 5α,6β-dichlorocholestan-3β -yl acetate and 5α,6β -dichlorocholestan- 3β -yl benzoate in methanol. |
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| ISSN: | 0352-5139 1820-7421 |