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Nucleophilic Addition of Enols and Enamines to α,β-Unsaturated Acyl Azoliums: Mechanistic Studies

Authors

  • Ramesh C. Samanta,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Biplab Maji,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13 (Haus F), 81377 München (Germany)
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  • Dr. Suman De Sarkar,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Dr. Klaus Bergander,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Dr. Roland Fröhlich,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Dr. Christian Mück-Lichtenfeld,

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Prof. Dr. Herbert Mayr,

    Corresponding author
    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13 (Haus F), 81377 München (Germany)
    • Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13 (Haus F), 81377 München (Germany)
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  • Prof. Dr. Armido Studer

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • This work was financially supported by the NRW International Graduate School of Chemistry (stipend to R.C.S.) and the Deutsche Forschungsgemeinschaft (SFB 749). We thank Prof. Stefan Grimme for providing the infrastructure for this work.

Abstract

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1,4 but not 1,2! The reactivity of 1 towards different nucleophiles (deprotonated β-diketones, enamines, and malonodinitrile) was investigated by NMR and kinetic experiments. These investigations proved that C[BOND]C bond formation occurs by a Michael-type 1,4-addition and not by a 1,2-addition and subsequent [3,3]-sigmatropic rearrangement. The first X-ray structure of an α,β-unsaturated acyl azolium salt (1) is also presented.

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