🥼organic chemistry review

Sigmatropic rearrangement

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025

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.