Sigmatropic rearrangement is a pericyclic rearrangement of bonds in which the one Ïƒ-bond gets changed into another Ïƒ-bond. The reaction is an intramolecular reaction in which the catalyst is absent. The number of bonds does not change after the rearrangement. The bonds shift their place without changing the number of electrons in the molecule. The rearrangements most frequently used include cope rearrangement, Carroll rearrangement, Claisen rearrangement, and the Fischer indole synthesis. Cope rearrangement involves the [3,3] shift of sigmatropic rearrangement of allyl vinyl ether or 1,5-dine. The Claisen rearrangement is very useful in a reaction where two carbon atoms form a bond. The Fischer indole synthesis is a reaction wherein an aromatic heterocycle indole is formed from phenylhydrazine reacting with an aldehyde or ketone.
A sigmatropic rearrangement is a type of pericyclic reaction where one Ïƒ-bond gets changed into another Ïƒ-bond in an intramolecular reaction in which the catalyst is absent. The total number of Ïƒ-bonds remains unchanged after the rearrangement. Hydrogen or its isotopes mostly undergo this type of rearrangement. The rearrangements that include the shifting of the bonds are shown by the curved arrows. One of the hydrogen shifts converts a very unstable allene into a conjugated triene. In this rearrangement reaction, one substituent moves from one side of the electron system to another part, simultaneously rearranging the electron system. This rearrangement is an intramolecular reaction. The sigmatropic rearrangement is mostly uncatalyzed, but few shifts may have the Lewis acid catalysis. The word sigmatropic has been derived from the Greek word tropos, which means to turn. In this rearrangement, the bond shifts its place without changing the number of electrons in the molecule. In analogous reactions, sigmatropic rearrangements mostly consist of a transition-metal catalyst that helps in forming the intermediate. The most frequently used rearrangements include Cope rearrangement, Carroll rearrangement, Claisen rearrangement, and the Fischer indole synthesis. Sigmatropic rearrangement can also be defined as the migration of a Ïƒ-bond and the atom replaced from their original location.
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