1α-endo-Dicyclopentadienyl vinyl ether undergoes Claisen rearrangement at 110°C, whereas at higher temperatures it suffered a tandem Claisen and Cope rearrangement. In contrast, the epimeric 1β- vinylether undergoes only Cope, and no Claisen rearrangement. In exo- dicyclopentadienyl series where there is no possibility of Cope rearrangement, only the α-vinylether underwent a smooth Claisen rearrangement.