Sigmatropic rearrangement

Definition

Sigmatropic rearrangement is a type of pericyclic reaction in organic chemistry where a sigma bond (σ-bond) adjacent to a pi system (π-system) migrates from one position to another, simultaneously affecting the positions of π-electrons. This migration is guided by specific orbital symmetries that allow the reaction to proceed without the need for external reagents.

Related terms

Pericyclic Reaction: A type of chemical reaction where bonds are formed or broken through concerted movements of electrons in cyclic systems.

Orbital Symmetry: The concept that describes how the symmetry properties of atomic orbitals affect the outcome and feasibility of chemical reactions.

Pi System (π: System) - A part of an organic molecule composed of alternating single and double bonds where π-electrons are delocalized over multiple atoms