Underlying Mechanism of The Birch Reduction
The original Birch mechanism suggested that the initial radical anion protonation was meta to the ring methoxy and alkyl groups and the last step, protonation of a cyclohexadienyl anion, was ortho. Birch’s original mechanism was based on qualitative reasoning, namely that the radical anion’s electron density, resulting from the addition of an electron, would become highest meta to an electron donor (such as methoxy or methyl) due to avoiding the usual ortho-para high density in the neutral species.
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