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Reactions of 5α-hydroxy steroids : IX. The acid catalysed rearrangement of 4β-acetoxy-5α-oxygenated cholestanes.

✍ Scribed by J.M. Coxon; M.P. Hartshorn

Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
203 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Westphalen rearrangement' of 38,68-substituted-cholestan-5u-ols

(1)

to give 5g-methyl-A'-compounds

(2) has received considerable study2.

No rearrangement products are obtained from 5J3-hydroxy-3, 6a-substituted-4, 6f3-methyl-5 or 6-keto-derivatives 6 . Recently Davies and Summers' reported the

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✍ J.M. Coxon; M.P. Hartshorn; C.N. Muir; K.E. Richards 📂 Article 📅 1967 🏛 Elsevier Science 🌐 French ⚖ 266 KB

The greater yield (61%) of the 6-ketone (2a) from 3a-acetoxy-5,6a-epoxy-5a-cholestane (la) compared with the yield (34%) of B-ketone (2b) from the corresponding 3-deoxy compound has been ascribed' to the energetically favourable conformational change, involving the 3-acetoxy group, in the formation

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Snatzlce and Pehlhaber' reported the isolation, in yields up to 5C$, of an unsaturated diaoetate on treatment of the triacetate (I) with acetic anhydride in the presence of a variety of acidic catalysts at 80' or 440'. Theee authors tentatively assigned structure (II) to the diacetate but later comm