Epoxidation of 2,3-Dimethylbenzo[b]furans by Dimethyldioxirane
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Adam, W.
Bialas, J.
Hadjiarapoglou, L.
Sauter, M.
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VCH Verlagsgesellschaft
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peer reviewed
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Chem. Ber.
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The synthesis of epoxides 2 by the reaction of the chloro- and methyl-substituted 2,3-dimethy1benzofurans l with dimethyl-dioxirane at low temperature is reported. These labile epoxides were spectroscopically characterized (1H and 13C NMR) at subambient temperatures. Epoxidation of benzofuran l c affords a 31:69 mixture of epoxide 2c and quinone methide 3c, the latter presumably being produced by valence isomerization of the epoxide. On Warming up above 10Β°C, the epoxides 2 suffer decomposition. Treatment of epoxide 2i with methanol yields the tautomeric mixture of adducts 4i and 4i'.
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Epoxidation / Dioxirane, dimethyl / Benzofurans, 2,3-dimethy1- / Benzofuran epoxides / Quinone methides / Methanol addition
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https://docs.google.com/file/d/0BxfLht5wJUEIMDgxYjFmMDItMWQxMy00MTA5LWEzNTktYjU4OTJiZjkxYjZi/edit?hl=en
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en
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας