title: Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides.
abstract: 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 H2O2were 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.
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida, USA.
authors.forename: Gabriel
authors.identifier: 0000-0002-8235-5969
authors.initials: G
authors.lastname: Dos Passos Gomes
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.|Faculty of Chemical and Pharmaceutical Technology and Biomedical Products, D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow, 125047, Russia.|All-Russian Research Institute for Phytopathology, 143050 B, Vyazyomy, Moscow Region, Russia.
authors.forename: Ivan A
authors.identifier: 0000-0003-1068-9051
authors.initials: IA
authors.lastname: Yaremenko
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.|All-Russian Research Institute for Phytopathology, 143050 B, Vyazyomy, Moscow Region, Russia.
authors.forename: Peter S
authors.initials: PS
authors.lastname: Radulov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.
authors.forename: Roman A
authors.initials: RA
authors.lastname: Novikov
authors.affiliation: Department of Chemistry, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory, Moscow, 119991, Russian Federation.|A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Leninsky prosp. 31, 119991, Moscow, Russian Federation.
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Chernyshev
authors.affiliation: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova st, Moscow, 119991, Russian Federation.
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Korlyukov
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.
authors.forename: Gennady I
authors.initials: GI
authors.lastname: Nikishin
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida, USA.
authors.forename: Igor V
authors.identifier: 0000-0001-9289-3819
authors.initials: IV
authors.lastname: Alabugin
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.|Faculty of Chemical and Pharmaceutical Technology and Biomedical Products, D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow, 125047, Russia.|All-Russian Research Institute for Phytopathology, 143050 B, Vyazyomy, Moscow Region, Russia.
authors.forename: Alexander O
authors.identifier: 0000-0001-8018-031X
authors.initials: AO
authors.lastname: Terent'ev
keywords: anomeric effect; ozonides; peroxides; stereoelectronic control; synthetic methods