Chloroalkyl 1,2-dioxolanes from unsaturated hydroperoxides and t-butyl hypochlorite

Article abstract of DOI:10.1016/S0040-4039(00)97247-2

Five monocyclic and one bicyclic 3-(1-chloroalkyl)-1,2-dioxolanes have been prepared by reaction of alk-3-en-1-yl hydroperoxides with t-butyl hypochlorite in CH₂Cl₂ in the presence of pyridine or silica; cyclooct-4-en-1-yl hydroperoxide with (t)BuOCl/SiO₂ regiospecifically affords 4-chlorocyclooctanone as major product.