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33747667919
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note
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3 in the presence of 1.0 M equiv of benzyltriethylammonium chloride over epoxide 1 in DMSO for 20 h at room temperature. Benzyltriethylammonium chloride was found to promote the oxidation of disubstituted aromatic epoxides and diols to corresponding aldehydes: Sayama, S. Unpublished results.
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33747681361
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note
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3 in the presence of 1,3-propanediol, accompanied by hydrobenzoin (60%). On the contrary, trans-4-chlorostilbene oxide was converted to 2-phenyl-1,3-dioxane 4a (81%) and 2-(4-chlorophenyl)-1,3-dioxane (81%) under the same reaction conditions. Consequently, trans-epoxides were more smoothly oxidized and converted to the corresponding 1,3-dioxanes by this method than cis-epoxides.
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33747703440
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note
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For bromoalcohol examples by alternative method, see Ref. 3c.
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33747668569
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3 in DMSO under the same reaction conditions. For the effect of benzyltriethylammonium chloride, see Ref. 9.
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52
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33747739229
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3 (9:1, v/v). 2-Phenyl-1,3-dioxane 4a (79 mg, 0.48 mmol) was obtained in 96% yield.
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