Studies on the Stability of Cycloprop-2-ene Carboxylate Dianions and Reactions with Electrophiles
Laural A. Fisher and Joseph M. Fox*
*Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, Email: jmfoxudel.edu
L. A. Fisher, J. M. Fox, J. Org. Chem., 2008, 73, 8474-8478.
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Dianions generated from alkyllithium reagents and cycloprop-2-ene carboxylic acids can be functionalized by electrophiles at the vinylic position. Due to reproducibility issues for reactions that were carried out in Et2O, a detailed study revealed that THF was a superior solvent. Additionally, it was found that the addition of NMO has a beneficial effect both on the stability of the dianions and on the rates of alkylation.
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V. Tarwade, X. Liu, N. Yan, J. M. Fox, J. Am. Chem. Soc., 2009, 131, 5382-5383.