Normal radical relay chlorination of cholestan-3α-ol
directed by an attached m-iodobenzoate ester group affords a
9α-chloro steroid, but when the same reaction is conducted in the
presence of an excess of CBr4 the product is a 9α-bromo
steroid. Similarly, when the same radical relay reaction is carried out
in the presence of an excess of (SCN)2 rather than
CBr4, the product is a 9α-thiocyano steroid. Several
other examples of these reactions have been developed. These tandem
remote functionalization reactions succeed because an intramolecular
hydrogen abstraction by a complexed-chlorine atom generates a specific
substrate radical in each case.
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Journal of the Chemical Society, Perkin Transactions 1
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