Über die Oxydation des O‐Methylbulbocapnins mit Jod

The oxidation product obtained by treatment of bulbocapnine methyl ether (2a) with iodine in ethanol/water is not the tetradehydroaporphinium salt 4 as assigned by Gadamer & Kuntze, but a dimer of structure 3. Reduction of 3 with zinc in dilute sulfuric acid gives rac‐bulbocapnine methyl ether,...

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Veröffentlicht in:Helvetica chimica acta 1975, Vol.58 (1), p.185-189
Hauptverfasser: Gerecke, Max, Borer, René, Brossi, Arnold
Format: Artikel
Sprache:eng
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Zusammenfassung:The oxidation product obtained by treatment of bulbocapnine methyl ether (2a) with iodine in ethanol/water is not the tetradehydroaporphinium salt 4 as assigned by Gadamer & Kuntze, but a dimer of structure 3. Reduction of 3 with zinc in dilute sulfuric acid gives rac‐bulbocapnine methyl ether, whereas reduction with complex hydrides affords the diastereomeric dimers 7a and 7b.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19750580124