Functionalized Ozonides by Substitution Reactions of Chlorinated Ozonides with Difunctional Alcohols

Substitution of 3‐chloro‐3,5‐bis(chloromethyl)‐5‐methyl‐1,2,4‐trioxolane ( 3 ) with allyl alcohol gave the corresponding diastereomeric allyloxy‐substituted ozonides 4 , which were converted into diozonides 7 by ozone treatment. Substitutions of 3 with ethanediol or with 1,3‐propanediol gave the corresponding hydroxyalkoxy‐substituted ozonides 8, 14 , which were oxidized to the corresponding aldehydes 10, 16 . Reaction of 3,5‐dichloro‐3,5‐bis(chloromethyl)‐1,2,4‐trioxolane ( 1a ) with ethanediol gave the corresponding bis(hydroxy)‐substituted ozonide 19 as well as a bicyclic ozonide 18 by reaction of 1a with ethanediol in a ratio of 1:1.