Categories: C-O Bond Formation >
Synthesis of Peroxides
Name Reactions
Recent Literature
With an easily accessible cinchona alkaloid catalyst, efficient enantioselective
peroxidation and epoxidation have been successfully developed. Employing readily
available α,β-unsaturated ketones and hydroperoxides, this novel reaction will
open new possibilities in the asymmetric synthesis of chiral peroxides and
epoxides.
X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc., 2008,
130, 8134-8135.
Ketones or ketals were readily converted into the corresponding gem-dihydroperoxides
in high yields by treatment with ethereal H2O2 at ambient
temperature in the presence of phosphomolybdic acid (PMA) as catalyst.
Y. Li, H.-D. Hao, Q. Zhang, Y. Wu, Org. Lett., 2009,
11, 1615-1618.
Y. Li, H.-D. Hao, Q. Zhang, Y. Wu, Org. Lett., 2009,
11, 1615-1618.
Among various rhenium catalysts, Re2O7 in CH3CN
is a remarkably efficient and mild catalyst for the peroxyacetalization of
ketones, aldehydes, or acetals by H2O2 to generate
1,1-dihydroperoxides.
P. Ghorai, P. H. Dussault, Org. Lett.,
2008,
10, 4577-4579.
Ketones reacted with hydrogen peroxide in the presence of iodine to yield gem-dihydroperoxides
in acetonitrile and hydroperoxyketals in methanol in good yields. Aromatic
aldehydes were also converted to gem-dihydroperoxides in acetonitrile and
to hydroperoxyacetals in methanol.
K. Žmitek, M. Zupan, S. Stavber, J. Iskra, J. Org. Chem., 2007,
72, 6534-6540.
In the presence of catalytic amounts of
phosphomolybdic acid (PMA), ethereal hydrogen peroxide reacted readily with a
range of epoxides at ambient temperature, giving corresponding β-hydroxyhydroperoxides
in good yields.
Y. Li, H.-D. Hao, Y. Wu, Org. Lett., 2009,
11, 2691-2694.
Re2O7 is a mild and efficient catalyst for the
high-yielding condensation of 1,1-dihydroperoxides with ketones or aldehydes to
form 1,2,4,5-tetraoxanes. When applied in tandem with a Re(VII)-catalyzed
synthesis of 1,1-dihydroperoxides, the reaction provides a high-yielding one-pot
conversion of ketones or aldehydes to tetraoxanes.
P. Ghorai, P. H. Dussault, Org. Lett., 2009,
11, 213-216.
P. Ghorai, P. H. Dussault, Org. Lett., 2009,
11, 213-216.
