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Abstract
Methyl 4-tert-butylcyclohex-1-enecarboxylate undergoes 1 F reduction at a mercury cathode in DMF solution to give as the major single product a hydrodimer in which the cyclohexyl rings are joined axially and the methoxycarbonyl groups are also axial. The structure is confirmed by X-ray crystallography. Kinetic experiments, combined with force field calculations, indicate radicalanion/radical-anion coupling which is under stereoelectronic control and which dictates diaxial coupling of the cyclohexyl rings. Protonation of the resulting dimeric dianion is under thermodynamic control.
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