Effect of 11β-substituents on the regioselective chlorination of estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone

Article abstract of DOI:10.1016/0039-128X(94)90065-5

The reaction of 11β-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 11β-substituent, regioselectivity is lost, resulting in a mixture of 10β- and ortho-chlorinated products.Keywords: estradiol derivative; regioselective chlorination; 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone