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Microwave-Assisted Isomerizations of Epoxides to Allylic Alcohols

[ Vol. 15 , Issue. 5 ]


Gabriella Barozzino-Consiglio and Alessandro Mordini*   Pages 447 - 454 ( 8 )


The present work reports a study on the isomerization reactions of several alkyl epoxides to the corresponding allylic alcohols or bicyclic alcohols under microwave irradiation. The reaction occurred in the presence of lithium diisopropylamide as a base and different experimental conditions in terms of solvent, amount of the base, times and temperatures. The traditional heating with an oil-bath and the use of alternative organometallic bases, as the Lochmann-Schlosser bases, have been furthermore compared with the microwave heating. The results obtained show that the use of microwave irradiations on promoting the isomerization of epoxides gives access to a series of synthetically useful products, among which allylic alcohols and bicyclic alcohols, depending on the starting substrate.


Microwave irradiation, epoxides, allylic alcohols, isomerization reactions, lithium diisopropylamide, superbases.


Dipartimento di Chimica , Dipartimento di Chimica

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