In organic chemistry, a pericyclic reaction is a type of organic reaction wherein the transition state of the molecule has a cyclic geometry, and the reaction progresses in a concerted fashion. Pericyclic reactions are usually rearrangement reactions. The major classes of pericyclic reactions are:
| Name | Bond changes | |
|---|---|---|
| Sigma | Pi | |
| Electrocyclic reaction | + 1 | -1 |
| Cycloaddition | +2 | -2 |
| Sigmatropic reaction | 0 | 0 |
| Group transfer reaction | + 1 | -1 |
| Cheletropic reaction | + 2 | - 2 |
| Dyotropic reaction | 0 | 0 |
In general, these are considered to be equilibrium processes, although it is possible to push the reaction in one direction by designing a reaction by which the product is at a significantly lower energy level; this is due to a unimolecular interpretation of Le Chatelier's principle. Pericyclic reactions often have related stepwise radical processes associated with them. Some pericyclic reactions, such as the cycloaddition, are 'controversial' because their mechanism is not definitively known to be concerted (or may depend on the reactive system). Pericyclic reactions also often have metal-catalyzed analogs, although usually these are also not technically pericyclic, since they proceed via metal-stabilized intermediates, and therefore are not concerted.
A large photoinduced hydrogen sigmatropic shift was utilized in a corrin synthesis performed by Albert Eschenmoser containing a 16π system.
Due to the principle of microscopic reversibility, there is a parallel set of "retro" pericyclic reactions, which perform the reverse reaction.
Read more about Pericyclic Reaction: Pericyclic Reactions in Stereochemistry, Pericyclic Reactions in Biochemistry
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