A-Substituted 5β-Steroids. VII. The Polyhalogenation of 5β-Cholestan-2-one
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概要
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The polyhalogenation of 5β-cholestan-2-one (I) in acetic acid containing hydrogen halide occurs in this positional order: C<SUB>1</SUB>→C<SUB>3</SUB>→C<SUB>3</SUB> and finally at C<SUB>1</SUB>, which has the largest steric hindrance. The tetrahalogenation of the ketone (I) yields 1,1,3,3-tetrachloro-5β-cholestan-2-one (IXb), but fails to give the tetrabromo derivative; rather, it yields 1β,3,3-tribromo-5β-cholestan-2-one (Va), 1,1,3-tribromo-5β-cholest-3-en-2-one (VIIIa), and 1β,3-dibromo-5β-cholest-3-en-2-one (VIa). The conformations of the dihalo-, the trihalo-, and the tetrachloroketone derivatives are discussed in connection with the ORD, CD, IR, and NMR spectra.
- 公益社団法人 日本化学会の論文
著者
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Horiuchi C.
Department Of Chemistry Rikkyo (st. Paul's) University
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Horiuchi C.
Department of Chemistry, St. Paul's (Rikkyo) University
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Hagitani Akira
Department of Chemistry, College of Science, Rikkyo (St. Paul's) University
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Satoh J.
Department of Chemistry, Rikkyo (St. Paul's) University
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