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Updated: Jul 12, 2026

Spatial Separation of Molecular Conformers and Clusters
Published on: January 9, 2014
Mechanistic implications in the Morita-Baylis-Hillman alkylation: isolation and characterization of an intermediate
Marie E Krafft1, Thomas F N Haxell, Kimberly A Seibert
1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, 32306, USA. mek@chem.fsu.edu
Abstract:
An intermediate phosphonium salt has never been isolated from the Morita-Baylis-Hillman (MBH) reaction. Due to the weakly basic counterion produced in the MBH alkylation and allylation reactions, the reaction can be stopped after electrophilic attack on the zwitterionic enolate and an intermediate isolated. Upon analysis of the crystal structure, a trans geometry is observed, suggesting that there is no electrostatic interaction between phosphorus and oxygen in the zwitterionic enolate that undergoes alkylation, thus giving new mechanistic insight into the MBH reaction.
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