Isomerization studies: III. decarbonylation of oleoyl chloride preparation of C19 dicarboxylic acids

Abstract

AbstractMixtures of siomeric C17 diene hydrocarbons were obtained when oleoyl chloride was decarbonylated in the presence of a transition metal catalyst. The choice of catalyst determined the composition of diene mixture produced. Diene mixtures were characterized as a mixture of conjugated and 1,4‐ dienes, or as a mixture of isolated double bond dienes. Carboxylation of the conjugated C17 diene by hydroformylationoxidation procedure gave a C18 monocarboxylic acid as the major product, whereas with nonconjugated C17 diene, the major product was a C19 dicarboxylic acid. Application of the Koch carboxylation procedure to C17 diene mixtures gave a C19 dicarboxylic acid mixture as the major product. This latter acid mixture was structurally different from diacids obtained from the hydroformylation‐oxidation procedure.