A novel reactivity of SeO(2) with 1,3-dienes: formation of syn 1,2- and 1,4-diols via a facile C-Se bond oxidation |
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| Authors: | Nguyen T M Lee D |
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| Affiliation: | Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA. |
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| Abstract: | [reaction: see text] A novel reaction between 1,3-dienes and selenium dioxide to give syn 1,2- and 1,4-diol cyclic selenites was studied in detail. This study indicates that an initial concerted [4 + 2] cycloaddition followed by a stereospecific carbon-selenium bond oxidation is involved in this unprecedented syn dihydroxy addition reaction mediated by selenium dioxide. |
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