Effect of 11 beta-substituents on the regioselective chlorination of estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone.
The reaction of 11 beta-substituted estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone affords exclusively ortho-substituted monochlorinated products including a major 4-chloro and a minor 2-chloro derivative. In the absence of an 11 beta-substituent, regioselectivity is lost, resulting in a mixture of 10 beta- and ortho-chlorinated products.
Ali
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MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Québec, Canada.
van Lier
J E
JE
D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004958:Estradiol / Q000737:chemistry; D004967:Estrogens / Q000737:chemistry*; D001556:Hexachlorocyclohexane / Q000031:analogs & derivatives* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011809:Quinones / Q000737:chemistry*
D004967:Estrogens; D007202:Indicators and Reagents; D011809:Quinones; C090614:2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone; D004958:Estradiol; D001556:Hexachlorocyclohexane