Unexpected Cleavage of Crown Ether in the Reaction of Methyloxirane with K-,K+(15-crown-5)2

Unexpected Cleavage of Crown Ether in the Reaction of Methyloxirane with K-,K+(15-crown-5)2

Cleavage of oxirane and crown ether rings occurs when the supramolecular complex K-,K+(15-crown-5)2 reacts with methyloxirane in tetrahydrofuran solution. Potassium isopropoxide and potassium tetraethylene glycoxide vinyl ether are the main products of the reaction. The cleavage of 15-crown-5 is obs...

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Veröffentlicht in:Journal of organic chemistry 1999-12, Vol.64 (25), p.8990-8994
Hauptverfasser: Grobelny, Zbigniew, Stolarzewicz, Andrzej, Czaja, Monika, Demuth, Wolfgang, Maercker, Adalbert
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container_issue 25
container_start_page 8990
container_title Journal of organic chemistry
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creator Grobelny, Zbigniew
Stolarzewicz, Andrzej
Czaja, Monika
Demuth, Wolfgang
Maercker, Adalbert
description Cleavage of oxirane and crown ether rings occurs when the supramolecular complex K-,K+(15-crown-5)2 reacts with methyloxirane in tetrahydrofuran solution. Potassium isopropoxide and potassium tetraethylene glycoxide vinyl ether are the main products of the reaction. The cleavage of 15-crown-5 is observed also in the reaction of the metal complex with methyl iodide. That means that the crown ether acts both as an activator and as a reagent in these processes. The solvent was inert in the studied systems.
doi_str_mv 10.1021/jo981687x
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title Unexpected Cleavage of Crown Ether in the Reaction of Methyloxirane with K-,K+(15-crown-5)2
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