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Relevant academic research and scientific papers

A facile catalyst-free synthesis of gem-dihydroperoxides with aqueous hydrogen peroxide

gem-Dihydroperoxides were easily obtained from the corresponding carbonyl compounds in high yields through a catalyst-free method with aqueous H 2O2 (35%) in 1,2-dimethoxyethane at room temperature.

Triflic acid-functionalized silica-coated magnetic nanoparticles as a magnetically separable catalyst for synthesis of gem-dihydroperoxides

Triflic acid-functionalized silica-coated magnetic nanoparticles [γ-Fe2O3@SiO2-TfOH] were readily prepared and identified as an effictive catalyst for the transformation of aldehydes or ketones into their corresponding gem-dihydroperoxides with 30% aqueous hydrogen peroxide. The catalyst was easily separated by magnetic decantation and the recovered catalyst was reused for seven cycles without significant loss of catalytic activity. Copyright

Efficient synthesis of gem-dihydroperoxides with molecular oxygen and anthraquinone under visible light irradiation with fluorescent lamp

We developed an efficient dihydroperoxidation protocol of various carbonyl compounds with molecular oxygen and anthraquinone in 2-propanol under visible light irradiation with a fluorescent lamp, which produced corresponding gem-dihydroperoxides in high yields.

An efficient synthesis of gem-dihydroperoxides with molecular oxygen and anthracene under light irradiation

A new efficient dihydroperoxidation protocol of a wide variety of carbonyl compounds with molecular oxygen, anthracene, and 2-propanol under light irradiation afforded their corresponding gem-dihydroperoxides in high yields.

Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum

Artemisinin-derived compounds play an integral role in current malaria chemotherapy. Given the virtual certainty of emerging resistance, we have investigated spiro-1,2-dioxolanes as an alternative scaffold. The endoperoxide functionality was generated by the SnCl4-mediated annulation of a bis-silylperoxide and an alkene. The first set of eight analogs gave EC50 values of 50-150 nM against Plasmodium falciparum 3D7 and Dd2 strains, except for the carboxylic acid analog. A second series, synthesized by coupling a spiro-1,2-dioxolane carboxylic acid to four separate amines, afforded the most potent compound (EC50 ～5 nM).

The effect of iodine on the peroxidation of carbonyl compounds

(Chemical Equation Presented) Peroxidation of ketones and aldehydes with iodine as a catalyst was studied. Ketones reacted with 30% aq hydrogen peroxide in the presence of 10 mol % of iodine to yield gem-dihydroperoxides in acetonitrile and hydroperoxyketals in methanol. The yield of hydroperoxidation of various cyclic ketones was 60-98%, including androstane-3,17-dione, while acyclic ketones were converted with a similar efficiency. Aromatic aldehydes were also converted to gem-dihydroperoxides with hydrogen peroxide and iodine as catalyst in acetonitrile and to hydroperoxyacetal in methanol, while the reactivity of aliphatic ones remained the same as in noncatalyzed reactions. tert-Butylhydroperoxide reacted in a similar manner, giving the corresponding perether derivatives. A study was also made of the relative kinetics of dihydroperoxidation from which the Hammet equation gave a reaction constant (ρ) of -2.76, indicating the strong positive charge development in the transition state and the important role of rehybridization in the conversion of hydroperoxyhemiketal to gem-dihydroperoxide. In acetonitrile, the iodine catalyst is apparently able to discriminate between the elimination of a hydroxy, methoxy, and hydroperoxy group and addition of water, methanol, and H2O2 to a carbonyl group.

A simple and efficient synthesis of gem-dihydroperoxides from ketones using aqueous hydrogen peroxide and catalytic ceric ammonium nitrate

Ketones were efficiently converted into the corresponding gem-dihydroperoxides in high yields within a short period of time on treatment with aqueous H2O2 (50%) in the presence of a catalytic amount of CAN in acetonitrile at room temperature.

Iodine as a catalyst for efficient conversion of ketones to gem-dihydroperoxides by aqueous hydrogen peroxide

Iodine has been shown to be an efficient catalyst for the selective dihydroperoxidation of ketones with aqueous hydrogen peroxide. Ketones were directly converted to their corresponding gem-dihydroperoxides using a "green" oxidant (30% aq H2O2) and a simple catalyst (iodine) under neutral conditions in acetonitrile. The yield of hydroperoxidation of various cyclic ketones was 60-98% including androstane-3,17-dione, and acyclic ketones were converted with a similar efficiency.

Synthesis of 1,2-dioxolanes by annulation reactions of peroxycarbenium ions with alkenes

(Chemical Equation Presented) The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.