Activation of hydrogen peroxide through hydrogen-bonding interaction with acidic alcohols: epoxidation of alkenes in phenol.
[reaction: see text] Electrophilic activation of hydrogen peroxide can be achieved in acidic alcohol solvents without the need for a metal catalyst. This concept is illustrated by the epoxidation of alkenes with H(2)O(2) employing phenol as a solvent. It is proposed that intermolecular hydrogen bonding between H(2)O(2) and phenol activates H(2)O(2) for oxygen-atom transfer. In this interaction, the role of phenol is purely catalytic.
Wahlen
Joos
J
Department of Interphase Chemistry, Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, B-3001 Heverlee, Belgium.
De Vos
Dirk E
DE
Jacobs
Pierre A
PA