Brook Rearrangement

Abstract

The Brook rearrangement is a base‐catalyzed intramolecular migration of a silyl group from a carbon atom to an oxygen anion via a mechanism involving a hypervalent pentacoordinate silicon species with retention of the configuration at the silicon atom and inversion of the configuration at the carbon atom. The Brook rearrangement falls into two types: the normal Brook rearrangement and the radical Brook rearrangement. Although the most common rearrangement is the [1,2] rearrangement (in α‐silyl alcohols), the migration of the silyl group to a longer distance has also been reported.