Depto. Química Orgánica

PERICYCLIC REACTIONS

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15/07/2017
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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.
These reactions are complex but they can be used for the creation of carbonyl groups.
Claisen Rearrangement
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The starting material is an appropriate vinyl of phenolic ether.
A vinyl ether can be easily prepared by Markovnikov addition of alcohols to alkynes.
Kind of magic! Isn't it?.
It takes a reorganization of the pi clouds and the cleavage/formation of sigma bonds.
Doesn't it remind you of the Diels-Alder reaction but in an intramolecular fashion?
Oxi-Cope Rearrangement
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If the double C=C bonds are placed in the appropriate position relative to an alcohol, the peryciclic reaction can give rise to an enol that immediately equilibrates with the corresponding keto form.