Issue 6, 1988

Steroidal allylic and homoallylic rearrangements during halogenation with triphenylphosphine and carbon tetrachloride

Abstract

Treatment of 3β-hydroxyandrost-5-en-17-one with triphenylphosphine and carbon tetrachloride under various conditions affords 3α- and 3β-chloroandrost-5-en-17-one, 3α,5-cycloandrost-6-en-17-one, and minor amounts of 17-dichloromethylene derivatives. In contrast, 4β-acetoxy-3β-hydroxyandrost-5-en-17-one affords 4β-acetoxy-3α-chloro- and 3β-acetoxy-4α-chloro-androst-5-en-17-ones. 3β-Acetoxy-4β-hydroxyandrost-5-en-17-one affords 3β-acetoxyandrost-4,6-dien-17-one and minor amounts of the 3β-acetoxy-4α-chloro-5-ene and 3β-acetoxy-6α-chloro-4-ene.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1469-1472

Steroidal allylic and homoallylic rearrangements during halogenation with triphenylphosphine and carbon tetrachloride

J. R. Hanson, P. B. Hitchcock, P. B. Reese and A. Truneh, J. Chem. Soc., Perkin Trans. 1, 1988, 1469 DOI: 10.1039/P19880001469

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