Synthesis of 1-hydroperoxy-1'-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers.
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.
Terent'ev
Alexander O
AO
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation. terentev@ioc.ac.ru
Platonov
Maxim M
MM
Krylov
Igor B
IB
Chernyshev
Vladimir V
VV
Nikishin
Gennady I
GI
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
C503429:1,2,4-trioxane; D000080:Acetals; D000962:Antimalarials; D037621:Artemisinins; D006571:Heterocyclic Compounds; D010545:Peroxides; D007455:Iodine; C031327:artemisinin