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Issue 18, 2007
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Electrophilicity parameters for 2-benzylidene-indan-1,3-diones—a systematic extension of the benzhydrylium based electrophilicity scale

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Abstract

Kinetics of the reactions of four 2-benzylidene-indan-1,3-diones (1a–d) with carbanions (2a–l) have been studied photometrically in dimethyl sulfoxide solution at 20 °C, and the electrophilicity parameters E were determined by the linear free energy relationship log k2(20 °C) = s(N + E) (eqn (1)). The rate-determining step of these reactions is the nucleophilic attack of the carbon nucleophile at the double bond of the Michael acceptor. Comparisons with literature data show that the linear free energy relationship (eqn (1)) allows the semiquantitative prediction of the reactivities of 2-benzylidene-indan-1,3-diones towards various nucleophiles.

Graphical abstract: Electrophilicity parameters for 2-benzylidene-indan-1,3-diones—a systematic extension of the benzhydrylium based electrophilicity scale

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Publication details

The article was received on 29 May 2007, accepted on 23 Jul 2007 and first published on 09 Aug 2007


Article type: Paper
DOI: 10.1039/B708025E
Org. Biomol. Chem., 2007,5, 3020-3026

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    Electrophilicity parameters for 2-benzylidene-indan-1,3-diones—a systematic extension of the benzhydrylium based electrophilicity scale

    S. T. A. Berger, F. H. Seeliger, F. Hofbauer and H. Mayr, Org. Biomol. Chem., 2007, 5, 3020
    DOI: 10.1039/B708025E

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