Tetrahedron Letters p. 5641 - 5644 (1995)
Update date:2022-08-05
Topics: NMR spectroscopy Catalyst Solvent Precursor Metalation Gas Chromatography Reactant Arylmethyl methyl ethers Reductive electrophilic substitution
Azzena, Ugo
Demartis, Salvatore
Fiori, Maria Giovanna
Melloni, Giovanni
Pisano, Luisa
Stable α-methoxy arylmethyl carbanions can be generated by metalation of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degC, avoiding Wittig rearrengement to the corresponding alkoxides 2.Reaction of these carbanions with various electrophiles afforded the expected products 3 in satisfactory yields.Connection between the metalation procedure and the reductive electrophilic substitution of arylmethyl methyl ethers allowed the transformation of compounds 1 into 2-arylpropanoic acids, 5.
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