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Synthesis of Peroxides

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Griesbaum Coozonolysis


Ozonolysis


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.


A highly enantioselective organocatalytic peroxidation of enals enabled an enantioselective route toward the core structure of interesting anticancer natural products including a cyclization cascade of a chiral bis(epoxy)hydroperoxide and should be applicable to the enantioselective synthesis of a broad range of chiral 1,2-dioxolanes and 1,2-dioxanes.
L. Hu, X. Lu, L. Deng, J. Am. Chem. Soc., 2015, 137, 8400-8403.


tert-Butylperoxyamido acetals can be generated in high yields under mild conditions via oxidative functionalization of C-H bonds adjacent to the amide nitrogen atom. Treatment with Grignard reagents enables the synthesis of α-substituted amides.
H. Yu, J. Shen, Org. Lett., 2014, 16, 3204-3207.


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.


A cobalt-catalyzed peroxidation of silyl enol ethers with molecular oxygen and triethylsilane provides silyl monoperoxyketals in good yield. These compounds serve as precursors to peroxycarbenium ions, which undergo annulations to provide 1,2-dioxolanes.
B. Hurlocker, M. R. Miner, K. A. Woerpel, Org. Lett., 2014, 16, 4280-4283.


A cobalt-catalyzed peroxidation of silyl enol ethers with molecular oxygen and triethylsilane provides silyl monoperoxyketals in good yield. These compounds serve as precursors to peroxycarbenium ions, which undergo annulations to provide 1,2-dioxolanes.
B. Hurlocker, M. R. Miner, K. A. Woerpel, Org. Lett., 2014, 16, 4280-4283.


Commercial, inexpensive 5-mm milliwatt light-emitting diodes are effective sources for batch microphotochemical oxidations using limited quantities of singlet oxygen. These atom economical oxidations are useful for labeling experiments with rare isotopes.
J. M. Carney, R. J. Hammer, M. Hulce, C. M. Lomas, D. Miyashiro, Synlett, 2012, 23, 2560-2566.


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.


Substituted oxiranes were readily transformed to the corresponding β-hydroxyhydroperoxides in good yields in ethereal H2O2 system with SnCl4 as a catalyst. Alternatively, the use of a stoichiometric amount of SnCl4 leads to a rearrangement of the oxiranes to aldehydes. A subsequent addition of ethereal H2O2 solution achieves primary gem-dihydroperoxides in moderate yields.
X. Yan, C. Qiao, Z. Guo, Synlett, 2013, 24, 502-506.


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.


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.


The acid-catalyzed reaction of β,δ-triketones with hydrogen peroxide produces tricyclic peroxides selectively in good yields via the monoperoxidation of the carbonyl groups in β-position and the transformation of the δ-carbonyl group into an acetal. The resulting peroxides can be easily isolated from the reaction mixture.
A. O. Terent'ev, I. A. Yaremenko, V. V. Chernyshev, V. M. Dembitsky, G. I. Nikishin, J. Org. Chem., 2012, 77, 1833-1842.