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Issue 92, 2018
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An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst

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Abstract

The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C–C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Brønsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.

Graphical abstract: An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst

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Publication details

The article was received on 10 Sep 2018, accepted on 19 Oct 2018 and first published on 19 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07329E
Citation: Chem. Commun., 2018,54, 12970-12973

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    An efficient method for retro-Claisen-type C–C bond cleavage of diketones with tropylium catalyst

    M. A. Hussein, V. T. Huynh, R. Hommelsheim, R. M. Koenigs and T. V. Nguyen, Chem. Commun., 2018, 54, 12970
    DOI: 10.1039/C8CC07329E

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