Photooxygenation of 1-Alkyl-2,3-diarylcyclopropanes via Photoinduced Electron Transfer: Stereoselective Formation of 4-Alkyl-3,5-diaryl-1,2-dioxolanes and Their Conversion to 1,3-Diols

Article abstract of DOI:10.1021/jo00300a024

The 9,10-dicyanoanthracene-sensitized photooxygenation of 1-alkyl-2,3-diarylcyclopropanes in CH3CN afforded c-4-alkyl-r-3,t-5-diaryl-1,2-dioxolanes in excellent yields with high stereoselectivity, which upon hydrogenolysis on Pd-charcoal gave quantitatively the corresponding 1,2-threo-2,3-erythro-2-alkyl-1,3-diaryl-1,3-diols.