Radiation-initiated addition of acetaldehyde to allylalcohol and conversion of the 1:2-telomer into 1-methyl-2,8-dioxabicyclo[4,2,1]nonane

Abstract

Radiation-initiated addition of acetaldehyde to allyl alcohol gave a mixture of 5-hydroxy-2-pentanone (1:1-adduct I), 2-methyl-2-(4-oxopentyloxy)tetrahydrofuran (II), 7-hydroxy-4-hydroxymethyl-2-heptanone (1:2-telomer III) and 1,1-bis(4-oxopentyloxy)ethane (IV). The telomer III was dehydrated to afford 3-acetonyltetrahydropyran (IV), 1-methyl-2,8-dioxabicyclo[4.2.1]nonane (VI) and 3,10-dimethyl-4,11,16,17-tetraoxatricyclo[8.4.2.23,8]octadecane (VII).