A Simple Synthesis of Macrocyclic Hydrocarbons by Metathesis of Cycloolefins

Article abstract of DOI:10.1055/s-1987-28129

Metathesis of cycloolefins normally leads to unsaturated polymers.Using rheniumheptoxide on alumina, activated by tintetramethyl and working in dilution via soxhlet-similiar circulation system the metathesis reaction was directed to macrocyclic dienes, which are the dimers of the initial cyclolefins.Starting with C7-, C9- and C10-cycloolefins symmetric macrocyclic C14-, C18- and C20-dienes are obtained in yields of 58-74percent.The metathetic dimerization of cyclooctene leads to 1,9-cyclohexadecadiene in a yield of 30percent.By hydrogenation at room temperature and normalhydrogen-pressure all cyclodienes were converted quantitatively to cycloalkenes (catalyst: potassium on alumina) or to cycloalkanes (catalyst: palladium on carbon).