Issue 45, 2008

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

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

Supplementary files

Article information

Article type
Communication
Submitted
18 Jul 2008
Accepted
29 Sep 2008
First published
14 Oct 2008

Chem. Commun., 2008, 6054-6056

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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