Classical Examples
The Nazarov cyclization reaction is a named electrocyclic reaction converting divinylketones to cyclopentenones.
A classic example is the thermal ring-opening reaction of 3,4-dimethylcyclobutene. The cis isomer exclusively yields cis,trans-2,4-hexadiene whereas the trans isomer gives the trans,trans diene :
This reaction course can be explained in a simple analysis through the frontier-orbital method: the sigma bond in the reactant will open in such a way that the resulting p-orbitals will have the same symmetry as the HOMO of the product (a butadiene). The only way to accomplish this is through a conrotatory ring-opening which results in opposite signs for the terminal lobes.
Read more about this topic: Electrocyclic Reaction
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