Electrocyclic Reaction - Classical Examples

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

Famous quotes containing the words classical and/or examples:

    Et in Arcadia ego.
    [I too am in Arcadia.]
    Anonymous, Anonymous.

    Tomb inscription, appearing in classical paintings by Guercino and Poussin, among others. The words probably mean that even the most ideal earthly lives are mortal. Arcadia, a mountainous region in the central Peloponnese, Greece, was the rustic abode of Pan, depicted in literature and art as a land of innocence and ease, and was the title of Sir Philip Sidney’s pastoral romance (1590)

    No rules exist, and examples are simply life-savers answering the appeals of rules making vain attempts to exist.
    André Breton (1896–1966)