Vinylcyclopropyl TMM diyls: access to eight-membered rings

Vinylcyclopropyl substituted diazenes (e.g. 1 and 15) rearrange when heated. The chemistry takes place via the formation of a trimethylenemethane (TMM) diyl and provides access to eight-membered rings. When the cyclopropane is fused to a five-membered ring (e.g. 15) rearrangement leads to a structure resembling the taxotere framework.