Thermal Isomerisation of Cyclic cis, trans, cis-Trienes

Article abstract of DOI:10.1021/jo00317a008

The thermal isomerisation of a series of cyclic conjugated cis, trans, cis-trienes was examined.The results obtained show a structure-reactivity correlation between the size of the ring vs. the type of product observed.The eleven-membered-ring triene (4) yields a novel tricyclic isomer 8, whereas the nine-membered-ring triene (5) yields the bicyclic diene 9.The ten-membered analogue 3 yields a mixture of both types of observed products.Mechanistic possibilities are proposed to explain the formation of both types of products.