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.
[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.
Nguyen
T M
TM
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Lee
D
D
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D018036:Selenium Compounds / Q000737:chemistry*; D064588:Selenium Oxides
D000438:Alcohols; D000475:Alkenes; D016566:Organoselenium Compounds; D018036:Selenium Compounds; D064588:Selenium Oxides