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Gerüstumlagerung eines α,β -ungesättigten γ,δ-Epoxiketons bei der Birch-Reduktion: Strukturaufklärung mittels 13C-INADEQUATE-NMR-Spektroskopie

✍ Scribed by Wolfgang Kreiser; Voker Rüschenbaum; Hans Bauer; Joachim Buddrus


Book ID
102254115
Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
245 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

Skeleton Rearrangement of an α‐β‐Unsaturated γ,δ‐Epoxyketone during Birch Reduction: Structure Elucidation by Means of ^13^C‐INADEQUATE‐NMR Spectroscopy

When the γ‐epoxide 2 of β‐ionone is treated under standard Birch‐reduction conditions, unexpectedly a 70% combined yield of regioisomeric octalones 4 and 5 is isolated. These products unquestionably result form cleavage of the central epoxide CC bond. The structure of compounds 4 and 5 could be determined by means of ^13^C‐INADEQUATE‐NMR spectroscopy.