Electroorganic Synthesis. 65. Anodic Homocoupling of Carboxylic Acids Derived from Fatty Acids.
作者:Andreas Weiper-Idelmann、Martin aus dem Kahmen、Hans J. Schäfer、Marianne Gockeln、Per Halfdan Nielsen、Ask Püschl、Kurt V. Mikkelsen、Alexander Senning
DOI:10.3891/acta.chem.scand.52-0672
日期:——
Fatty acid derived carboxylic acids with double bonds, hydroxy-, amino-, keto-, ester- and epoxy groups are anodically coupled to dimers (Kolbe electrolysis) in 29 to 81% yield and up to a 2.5 mol scale. Problems due to the low conductivity of fatty acid salts were overcome by the use of a how cell with a narrow electrode gap. Fatty acids with branched alkyl chains gave dimers with interesting emulsifying properties. Dimethyl hexadecanedioate, accessible from methyl azelate, could be cyclized and further converted into homomuscone and muscone in a few steps. A commercial mixture of dimeric fatty acids (C-36-dicarboxylic acids) has been coupled to give C-70-diesters.