Abstract
Reaction conditions for improved dimer yields in the Kolbe-electrolysis of β,γ-unsaturated carboxylic acids are examined. With vinylacetic acid ( 1) the passivation could not be lowered by decreasing neutralization, changing the anode from platinum to graphite and the solvent to methanol: pyridine, by adding p-toluenesulfonate and formate as spacers or hydroquinone as inhibitor; 1,5-hexadiene was not detectable. Shielding the double bond reduced the passivation but still yielded no dimer; shifting the double bond into γ,δ-position afforded with 2-cyclohexenylacetic acid ( 8) 8% dimer. When however 1 was neutralized with (C 4H 9) 3N or 8 with (C 2H 5) 3N at lower passivation 31% dimer was obtained.
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