Epoxidation of Alkenes with Peracids
Epoxidation of Alkenes with Peracids: Influence of OH Groups
Because of hydrogen bonding between the hydroxyl group and the attacking peracid in the transition state, it has been suggested that hydroxyl groups have a directive effect during epoxidation. The peracid preferrably attacks the alkene from the side at which the hydroxyl group resides.
1,2-Epoxy-3-hydroxycyclohexane (click for 3D model).