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

Kreiser Wolfgang | Zendy; Rüschenbaum Voker | Zendy; Bauer Hans | Zendy; Buddrus Joachim | Zendy

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

Author(s) -

Kreiser Wolfgang,

Rüschenbaum Voker,

Bauer Hans,

Buddrus Joachim

Publication year - 1984

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.19840670827

Subject(s) - chemistry , epoxide , nuclear magnetic resonance spectroscopy , yield (engineering) , birch reduction , spectroscopy , stereochemistry , cleavage (geology) , organic chemistry , catalysis , materials science , physics , geotechnical engineering , quantum mechanics , fracture (geology) , engineering , metallurgy

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 CC bond. The structure of compounds 4 and 5 could be determined by means of 13 C‐INADEQUATE‐NMR spectroscopy.

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