Die Isomerisierung von 5‐Methyl‐19‐nor‐koprosten‐Derivaten. I. Teil. Die Irreversibilität der  Westphalen‐Lettré ‐Umlagerung | Zendy

Aebli H. | Zendy; Grob C. A. | Zendy; Schumacher E. | Zendy

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Die Isomerisierung von 5‐Methyl‐19‐nor‐koprosten‐Derivaten. I. Teil. Die Irreversibilität der Westphalen‐Lettré ‐Umlagerung

Author(s) -

Aebli H.,

Grob C. A.,

Schumacher E.

Publication year - 1958

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.660410322

Subject(s) - chemistry , substituent , dehydration , yield (engineering) , medicinal chemistry , stereochemistry , biochemistry , materials science , metallurgy

Dehydration of 5‐hydroxy cholesterol derivatives is attended by C–10 to C–5 methyl migration ( Westphalen ‐ Lettré rearrangement) only if a β‐substituent is present at C–6. In the absence of such a substituent dehydration and dehydrochlorination of 5‐hydroxy and 5‐chloro derivatives respectively yield mainly 5‐cholestenes in a rate‐controlled 1,2‐elimination process.

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