1. Chemistry Department , Shiraz University , Shiraz, 71454, Iran;2. Chemistry Department , Shiraz University , Shiraz, 71454, Iran;3. Chemistry Department , Kermanshah University , Kermanshah, Iran
Abstract:
Ce(IV) as ceric ammonium nitrate can effectively catalyze ring opening of epoxides with halides under very mild conditions and easy procedure to give the corresponding β-chloro-and β-bromohydrins in excellent yields. The reactions occur with both substituted and unsubstituted quaternary ammonium halides and with high regio- and stereoselectivity. The reaction of optically active styrene oxide with chloride ion was found to be highly stereospecific and afforded the corresponding β-halohydrin in 96% ee.