Stereoelectronic Control in the Ozone‐Free Synthesis of Ozonides

• Published in: Angewandte Chemie International Edition Vol. 56; no. 18; pp. 4955 - 4959
• Main Authors: 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.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 24.04.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: anomeric effect; Carbon; Carbonyl compounds; Carbonyls; Chemistry; Chemistry, Multidisciplinary; Deactivation; Distortion; Guidelines; Hydrogen peroxide; Ozone; Ozonides; peroxides; Physical Sciences; Science & Technology; stereoelectronic control; synthetic methods; GEM-DIHYDROPEROXIDES; GEMINAL BISHYDROPEROXIDES; IODINE; peroxides; stereoelectronic control; DISPIRO-1,2,4,5-TETRAOXANES; ozonides; MILD; KETONES; BRIDGED 1,2,4,5-TETRAOXANES; anomeric effect; HYDROGEN-PEROXIDE; CYCLIC PEROXIDES; ARTEMISININ; synthetic methods

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 H2O2. The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2O2 were not detected...