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Issue 45, 2008
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A quantitative structure–reactivity relationship in decarboxylative Claisen rearrangement reactions of allylic tosylmalonate esters

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Abstract

First-order rate constants have been determined for the decarboxylative Claisen rearrangement reactions at 293 K of substituted methyl (E)-3-phenyl-2-propenyl 2-tosylmalonate esters, which show a linear free-energy relationship indicative of the development of positive charge on the benzylic position in the sigmatropic rearrangement transition-state.

Graphical abstract: A quantitative structure–reactivity relationship in decarboxylative Claisen rearrangement reactions of allylic tosylmalonate esters

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Publication details

The article was received on 18 Jul 2008, accepted on 29 Sep 2008 and first published on 14 Oct 2008


Article type: Communication
DOI: 10.1039/B812306C
Chem. Commun., 2008, 6054-6056

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    A quantitative structure–reactivity relationship in decarboxylative Claisen rearrangement reactions of allylic tosylmalonate esters

    D. Craig and N. K. Slavov, Chem. Commun., 2008, 6054
    DOI: 10.1039/B812306C

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