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Issue 3, 1997
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Remote functionalization by tandem radical chain reactions

Abstract

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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Article type: Paper
DOI: 10.1039/A600172F
Citation: J. Chem. Soc., Perkin Trans. 1, 1997, 339-348
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    Remote functionalization by tandem radical chain reactions

    D. Wiedenfeld, J. Chem. Soc., Perkin Trans. 1, 1997, 339
    DOI: 10.1039/A600172F

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