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One-electron Reduction




The first intermediate in a one-electron reduction is often a Radical Anion which then engages in secondary reactions. In the Birch Reduction the secondary reaction is proton abstraction from an Alcohol . This reaction type is also called a dissolving metal reduction. Alkyne reduction to an Alkene in the liquid Ammonia / Sodium system follows the same theme. The first radical anion intermediate abstracts a proton from ammonia to the Free Radical . A second one-electron transfer leads to the Anion which also abstracts a proton to the neutral alkene.

In the Wurtz Reaction two radical intermediates dimerize in a Coupling Reaction . Likewise acetone is converted to Pinacol with a magnesium - mercury Amalgam in a Pinacol Coupling reaction. Acyloin Condensation couples two Carboxylic Acid s to a α-hydroxyketone. Reactions of this type are also called reductive couplings. In the Clemmensen Reduction of ketones to alkanes with zinc-mercury amalgam the intermediate is an organozinc carbenoid.
Electron rich organic molecules like tetrakis(dimethylamino)ethylene (TDAE) are effective reducing agents capable of generating the Anion from Alkyl Halide s such as 5-chloromethyl-6-nitrobenzo {Link without Title} dioxole 1 .


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