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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.