The primary debate concerning the mechanism of the rearrangement centers on whether it is a concerted (sigmatropic) or stepwise (diradical) process. Mechanistic experiments have shown that trans-divinylcyclopropanes epimerize to the corresponding cis isomers and undergo the rearrangement via what is most likely a concerted pathway. A boat-like transition state has been proposed and helps explain the observed stereospecificity of the process. Whether the initial epimerization of trans substrates occurs via a one- or two-center process is unclear in most cases.
Transition-metal-catalyzed versions of the rearrangement are known, and mechanisms vary. In one example employing rhodium bis(ethylene) hexafluoroacetylacetonate, coordination and formation of a bis-π-allyl complex precede electrocyclic ring closure and catalyst release.