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The serini reaction

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Zusammenfassung

Der Mechanismus der Serini-Reaktion wird kurz erörtert und ein 17, 20-Oxyd als Zwischenprodukt vorgeschlagen. Das stereochemische Ergebnis der Reaktion soll von zwei Faktoren abhängig sein, und zwar: 1. von der Geometrie des « transition state » und 2. von der Konfiguration des Oxydrings. Ausgehend von diesen Überlegungen, kann vorausgesagt werden, daßReichsteins Substanz 0-Diacetat durch die Serini-Reaktion in ein 17-Iso-20-keton und nicht in ein 17-Normal-20-keton umgewandelt werden soll. Tatsächlich ist das 17-Isoallopregnanol-(3β)-on-20 als einziges Produkt experimentell aufgefunden worden.

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Literatur

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Authors and Affiliations

  1. The Chester Beatty Research Institute, The Royal Cancer Hospital, University of London, UK

    C. W. Shoppee

  2. University College, Swansea

    C. W. Shoppee

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  1. C. W. Shoppee
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Shoppee, C.W. The serini reaction. Experientia 4, 418–420 (1948). https://doi.org/10.1007/BF02144987

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