The Journal of Organic Chemistry

Birch reduction and reductive alkylation of benzonitriles and benzamides

AG Schultz, M Macielag

Index: Schultz, Arthur G.; Macielag, Mark Journal of Organic Chemistry, 1986 , vol. 51, # 25 p. 4983 - 4987

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Citation Number: 21

Abstract

When the nitrile-stabilized carbanion, loa, generated by Birch reduction of la was treated with NH4Cl rather than an alkyl halide, 2-cyano-l-methoxy-l, 3-cyclohexadiene (4) was obtained in 76% isolated yield. Diene 4 is stable to silica gel chromatography, and it successfully undergoes Diels-Alder reactions with a variety of dienophiles. Aryl esters 5a and 5b were prepared by cycloadditions of 4 to dimethyl acetylenedicarboxylate and ethyl ...