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Updated: May 5, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
McKenna reaction--which oxygen attacks bromotrimethylsilane?
1Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology , Zeromskiego 116, 90-924 Lodz, Poland.
Abstract:
The first experimental proof of the course of silylation in the McKenna reaction, one of the most widely used reactions for the synthesis of organophosphorus acids, is presented. The reaction (in acetonitrile) proceeds via an attack of the terminal oxygen from the dialkyl phosphonate on the silicon atom in bromotrimethylsilane. Isotopically enriched diethyl phenylphosphonates (P═(17)O or P═(18)O) were used as the model compounds. The location of the isotopic tracers was detected using (31)P and (17)O NMR spectroscopy.
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