Efficient Regioselective Opening of Epoxides by Nucleophiles in Water under Simultaneous Ultrasound/Microwave Irradiation

Abstract Epoxide cleavage by nucleophiles in aqueous media may suffer from competition by water itself, yielding the diol as byproduct. However, when the reaction was carried out under high-intensity ultrasound or microwaves, attack by the nucleophile was strongly promoted and water no longer reacte...

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Bibliographic Details
Published in:Synlett 2007-08, Vol.2007 (13), p.2041-2044
Main Authors: Palmisano, Giovanni, Tagliapietra, Silvia, Barge, Alessandro, Binello, Arianna, Boffa, Luisa, Cravotto, Giancarlo
Format: Article
Language:English
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Summary:Abstract Epoxide cleavage by nucleophiles in aqueous media may suffer from competition by water itself, yielding the diol as byproduct. However, when the reaction was carried out under high-intensity ultrasound or microwaves, attack by the nucleophile was strongly promoted and water no longer reacted. Best results were achieved under simultaneous ultrasound/microwave irradiation: a series of mono-, di- and trisubstituted oxiranes reacted rapidly with sodium azide or 1-(3-chlorophenyl)piperazine, usually leading to the corresponding more substituted alcohols in acceptable to high yields. This catalyst-free, greener protocol achieves a much faster cleavage of epoxides with a high regioselectivity.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-984891