Generation of Aryl- and Arylmethyl Carbanions by the Reductive Cleavage of Alkoxy-Substituted Aromatic Compounds

The reductive cleavage of the C-O bond of aryl- and arylmethyl alkyl ethers by electron trasfer from alkali metals in ethreal solvents was utilized to geneerate aryl- and arylmethyl carbanions. This procedure was successfully extended to different classes of alkoxy-substituted aromatic compounds, including derivatioves of aldehydes and ketones and heterocyclic compounds, thus allowing the genration of functionalized organometals. The usefullness of the procedure is illustrated with several examples, including the synthesis of antural products and pharmacologically active compounds.