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The rearrangement of 11,13-dibromo-9,10-dimethoxy-9,10-propanoanthracen-12-ones to the correspondingFavorskii products

Umlagerung von 11,13-Dibrom-9,10-dimethoxy-9,10-propanoathracen-12-onen zu den entsprechendenFavorskii-Produkten

  • Organische Chemie Und Biochemie
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Summary

Submittingcis- andtrans-11,13-dibromo-9,10-dimethoxy-9,10-propanoanthracen-12-one (4a,b) toFavorskii conditions (MeOH/KOH, 60°C) afforded theFavorskii ester5a and the α-keto acetal5b in 46% overall yield. Almost all reactions resulted in the formation of a single isomer which could be shown to be the most favored one by molecular mechanics calculations (MM2).

Zusammenfassung

UnterFavorskii-Bedingungen (MeOH/KOH, 60°C) entstehen auscis- undtrans-11,13-Dibrom-9,10-dimethoxy-9,10-propanoanthracen-12-on derFavorskii-Ester5a und das α-Keto-Acetal5b in 46% Gesamtausbeute. Fast alle Reaktionen ergeben ein einziges Isomeres, von dem mittels molekularmechanischer Berechnungen gezeigt werden konnte, daß es sich dabei um das energetisch günstigere Produkt handelt.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Assiut University, 71516, Assiut, Egypt

    A. A. O. Sarhan

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  1. A. A. O. Sarhan
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Sarhan, A.A.O. The rearrangement of 11,13-dibromo-9,10-dimethoxy-9,10-propanoanthracen-12-ones to the correspondingFavorskii products. Monatsh Chem 128, 79–83 (1997). https://doi.org/10.1007/BF00807641

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  • DOI: https://doi.org/10.1007/BF00807641

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