Ozone-Free Synthesis of Ozonides: Assembling Bicyclic Structures from 1,5-Diketones and Hydrogen Peroxide

• Published in: Journal of organic chemistry Vol. 83; no. 8; pp. 4402 - 4426
• Main Authors: Yaremenko, Ivan A, Gomes, Gabriel dos Passos, Radulov, Peter S, Belyakova, Yulia Yu, Vilikotskiy, Anatoliy E, Vil’, Vera A, Korlyukov, Alexander A, Nikishin, Gennady I, Alabugin, Igor V, Terent’ev, Alexander O
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.04.2018; Amer Chemical Soc
• Subjects: ambient temperature; chemical bonding; chemical reactions; Chemistry; Chemistry, Organic; hydrogen peroxide; Lewis acids; moieties; organic chemistry; organic compounds; Physical Sciences; Science & Technology; sulfuric acid; thermodynamics; DENSITY FUNCTIONALS; OXIDATION; DIMETHYL SULFIDE; KETONES; GEM-DIHYDROPEROXIDES; ACID; OZONOLYSIS; NONCOVALENT INTERACTIONS; ANTIMALARIAL; MICHAEL ADDITION

Reactions of 1,5-diketones with H2O2 open an ozone-free approach to ozonides. Bridged ozonides are formed readily at room temperature in the presence of strong Brønsted or Lewis acids such as H2SO4, p-TsOH, HBF4, or BF3·Et2O. The expected bridged tetraoxanes, the products of double H2O2 addition, we...