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Functionalized Ozonides by Substitution Reactions of Chlorinated Ozonides with Difunctional Alcohols

✍ Scribed by Griesbaum, Karl ;Quinkert, Ralf-Olaf

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
531 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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