1,2-Dioxolane versus 1,2-dioxane formation in the cyclization of an α,ω-diene hydroperoxide under polar and free radical conditions
Abstract
Radical cyclizations of 3-hydroperoxymethylhexa-1,5-diene occur exclusively at the C-1,C-2 double bond to afford 1,2-dioxolanes stereospecifically, whereas electrophile-induced cyclizations additionally yield products derived from attack at the C-5,C-6 double bond.