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A New α,β‐Enone → Alkynone Fragmentation. Syntheses of exaltone® and (±)‐muscone
Author(s) -
Fehr Charles,
Ohloff Günther,
Büchi George
Publication year - 1979
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.19790620815
Subject(s) - chemistry , electrophile , enone , fragmentation (computing) , yield (engineering) , catalysis , organic chemistry , ketone , medicinal chemistry , metallurgy , operating system , materials science , computer science
p ‐Toluenesulfonylhydrazones of α, β‐unsaturated ketones undergo an alkynone fragmentation in high yield when treated with electrophiles under basic conditions. With N ‐bromosuccinimide in alcohols, the p ‐tosylhydrazones 4a and 4b yielded in a one‐pot reaction the cyclic 4‐alkyn‐1‐ones 5a and 5b ; these were converted to Exaltone® ( 1a ) and muscone ( 1b ) on catalytic hydrogenation.