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Issue 17, 2008
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Nucleophilic reactivities of benzenesulfonyl-substituted carbanions

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Abstract

Kinetics of the reactions of four benzenesulfonyl-stabilized carbanions (1a–d) with reference electrophiles (quinone methides 2 and diarylcarbenium ions 3) have been determined in dimethyl sulfoxide solution at 20 °C in order to derive the reactivity parameters N and s according to the linear free-energy relationship log k(20 °C) = s(N + E) (eqn (1)). The additions of (1a–d) to ordinary Michael acceptors (e.g., benzylidene Meldrum's acid 4a, benzylidenebarbituric acids 5a–c, and benzylidene-indan-1,3-diones 6a–d) were also studied kinetically and found to be 5–24 times slower than predicted by eqn (1).

Graphical abstract: Nucleophilic reactivities of benzenesulfonyl-substituted carbanions

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Publication details

The article was received on 03 Apr 2008, accepted on 15 May 2008 and first published on 02 Jul 2008


Article type: Paper
DOI: 10.1039/B805604H
Org. Biomol. Chem., 2008,6, 3052-3058

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    Nucleophilic reactivities of benzenesulfonyl-substituted carbanions

    F. Seeliger and H. Mayr, Org. Biomol. Chem., 2008, 6, 3052
    DOI: 10.1039/B805604H

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