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New facts concerning the reaction of K, K(15-crown-5)2 with phenyl glycidyl ether: unexpected formation of potassium cyclopropoxide |
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| Authors: | Zbigniew Grobelny Andrzej Stolarzewicz Adalbert Maercker Wolfgang Demuth |
| Affiliation: | a Centre of Polymer Chemistry, Polish Academy of Sciences, 41-819 Zabrze, Poland b Institut für Organische Chemie, Universität Siegen, D-57068 Siegen, Germany |
| Abstract: | A new mechanism of the reaction of K−, K+(15-crown-5)2 with phenyl glycidyl ether is presented. The linear ether bond is attacked only to a small extent, if at all. As the main reaction path the oxirane bond in the β-position is cleaved, followed by the γ-elimination of potassium phenoxide and the formation of potassium cyclopropoxide. Crown ether ring opening also occurs in reactions with organometallic intermediates. |
| Keywords: | Potassium anion Phenyl glycidyl ether 15-Crown-5 Potassium cyclopropoxide |
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