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18.28: Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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JoVE Core
Organic Chemistry

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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
 
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18.28: Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion intermediates, the presence of an electron-withdrawing group stabilizes the ipso and para positions, favoring reduction at these positions. On the other hand, the presence of an electron-donating group stabilizes the ortho and meta positions, favoring reduction at these positions.

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Keywords: Birch Reduction Benzene 1,4-cyclohexadiene Solvated Electrons Radical Anion Cyclohexadienyl Radical Cyclohexadienyl Anion Electron-withdrawing Group Electron-donating Group Ipso Position Para Position Ortho Position Meta Position

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