title: Synthesis of 1-hydroperoxy-1'-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers.
abstract: It was found that iodine-catalyzed reactions of geminal bishydroperoxides with acetals proceed with the replacement of only one alkoxy group by the peroxide group to give previously unknown structures of 1-hydroperoxy-1'-alkoxyperoxides in yields up to 64%. The same compounds are formed in the iodine-catalyzed reactions of geminal bishydroperoxides with enol ethers. The nature of the solvent has a decisive influence on the formation of 1-hydroperoxy-1'-alkoxyperoxides. In the series of Et(2)O, THF, EtOH, CHCl(3), CH(3)CN, and hexane, the best results were obtained with the use of Et(2)O or THF as the solvent.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation. terentev@ioc.ac.ru
authors.forename: Alexander O
authors.initials: AO
authors.lastname: Terent'ev
authors.forename: Maxim M
authors.initials: MM
authors.lastname: Platonov
authors.forename: Igor B
authors.initials: IB
authors.lastname: Krylov
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Chernyshev
authors.forename: Gennady I
authors.initials: GI
authors.lastname: Nikishin
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000962:Antimalarials / Q000737:chemistry; D037621:Artemisinins / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C503429:1,2,4-trioxane; D000080:Acetals; D000962:Antimalarials; D037621:Artemisinins; D006571:Heterocyclic Compounds; D010545:Peroxides; D007455:Iodine; C031327:artemisinin