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note
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The epoxidation of homo- and bis-homoallylic alcohols and the ring-opening of the corresponding oxiranes in organic medium is often accompanied by the formation of hydroxy tetrahydrofuran and tetrahydropyran derivatives.17 In our case, the preparation of 1,2-epoxide 9 has been performed in water at pH 7.0 by oxidation of the corresponding alkene (10 mmol) with m-chloroperbenzoic acid (m-CPBA, 30 mmol), and the pH has been kept constant for the entire reaction time (2 h). With this procedure, we did not find any tetrahydrofuran or tetrahydropyrans derivatives as byproducts and the 5,6-epoxy-1-hexanol (9) has been obtained in 85% yield after workup of the reaction mixture.
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0028913329
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0142088370
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note
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In the first run, 1.5 equiv of thiophenol was used according to the standard procedure (see the Experimental Section). In the subsequent runs, 1.0 equiv of thiol was used and the reaction conversion was 100%.
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