Facile and selective procedure for the synthesis of bridged 1,2,4,5-tetraoxanes; strong acids as cosolvents and catalysts for addition of hydrogen peroxide to beta-diketones.
A facile, experimentally simple, and selective method was developed for the synthesis of bridged 1,2,4,5-tetraoxanes based on the reaction of hydrogen peroxide with beta-diketones catalyzed by strong acids (H(2)SO(4), HClO(4), HBF(4), or BF(3)). The yields of the target products vary from 44% to 77%. 1,2,4,5-Tetraoxanes can easily be separated from other reaction products by column chromatography. A high concentration of a strong acid is a key factor determining the selectivity of formation and the yield of 1,2,4,5-tetraoxanes. Unlike many compounds containing the O-O bond, which undergo rearrangements in acidic media, the resulting cyclic peroxides are quite stable under these conditions.
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
Borisov
Dmitry A
DA
Chernyshev
Vladimir V
VV
Nikishin
Gennady I
GI
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents / Q000737:chemistry*; D013379:Substrate Specificity; D045568:Tetraoxanes / Q000138:chemical synthesis* / Q000737:chemistry; D014961:X-Ray Diffraction
D000143:Acids; D007659:Ketones; D012997:Solvents; D045568:Tetraoxanes; D006861:Hydrogen Peroxide