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Stereoelectronic Control in the Ozone‐Free Synthesis of Ozonides
Author(s) -
dos Passos Gomes Gabriel,
Yaremenko Ivan A.,
Radulov Peter S.,
Novikov Roman A.,
Chernyshev Vladimir V.,
Korlyukov Alexander A.,
Nikishin Gennady I.,
Alabugin Igor V.,
Terent'ev Alexander O.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610699
Subject(s) - chemistry , ozone , ozonolysis , computational chemistry , combinatorial chemistry , organic chemistry , stereochemistry
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone‐free synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H 2 O 2 . The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H 2 O 2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three‐carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone.