118043-38-2Relevant articles and documents
Efficient regioselective opening of epoxides by nucleophiles in water under simultaneous ultrasound/microwave irradiation
Palmisano, Giovanni,Tagliapietra, Silvia,Barge, Alessandro,Binello, Arianna,Boffa, Luisa,Cravotto, Giancarlo
, p. 2041 - 2044 (2007)
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. Georg Thieme Verlag Stuttgart.
Solid-Supported Sodium Azide Reagents: Their Preparation and Reactions with Epoxides
Onaka, Makoto,Sugita, Keisuke,Izumi, Yusuke
, p. 1116 - 1123 (2007/10/02)
Sodium azide is supported on three types of porous solid acids (zeolite, alumina, and silica gel) and applied to several reactions with epoxides.A systematic investigation reveals that the reactivities of the supported reagents are greatly influenced by loading amounts of NaN3, amounts of adsorbed water in the reagents, acidic properties of the solid acids, and reaction solvents.For demonstrating the utility of supported NaN3 reagents in selective organic syntheses, nucleophilic ring-opening reactions of 2,3-epoxy alcohols with the supported reagents are examined.Among the supported reagents, only the Ca2+-exchanged zeolite-supported reagent induces a C-3 ring opening in a highly regioselective manner (>90percent).It is deduced that the role of calcium ions in the zeolite is to increase the acid strength of the zeolite facilitating the ring cleavage of epoxides and to fix the conformation of epoxy alcohols through forming chelate complexes with calcium ions.