Synthesis of gem-Dihydroperoxides from Ketones and Aldehydes Using Silica Sulfuric Acid as Heterogeneous Reusable Catalyst

Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN

“…Preparation of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane [46] Silica sulfuric acid (SSA) (100 mg) was added to a stirred solution of acetylacetone (100 mg, 1 mmol) in CH 3 CN (4 ml), and stirring of the reaction mixture was continued for 5 min at room temperature. Aqueous 30 % H 2 O 2 (5 mmol) was then added to the reaction mixture and stirring was continued for 30 min at room temperature.…”

“…We have synthesized trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane and used it as a new, powerful, solid and effective oxidant in organic synthesis [42][43][44][45][46]. So, in continuation of our interest in the application of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane, we report the use of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane-NH 4 ClHOAc for in situ generation of Cl ?…”

gem-Bishydroperoxides

“…[1][2][3][4][5] Apart from their biological activities, 6,7 gem-dihydroperoxides have been established as important building blocks in synthetic chemistry, for example the preparation of organic peroxides, trioxanes, tetraoxanes, spirobisperoxyketals, and dicarboxylic diesters. 4,7,8 gemDihydroperoxides can also be employed as oxidizing agents under various conditions to perform transformations such as epoxidation [1][2][3][4][5] and sulfoxidation. [2][3][4][5]9 In addition, in situ decomposition of gem-dihydroperoxides can generate singlet oxygen as the active oxidant 8,10 in olefin oxidation, for example.…”

“…4,7,8 gemDihydroperoxides can also be employed as oxidizing agents under various conditions to perform transformations such as epoxidation [1][2][3][4][5] and sulfoxidation. [2][3][4][5]9 In addition, in situ decomposition of gem-dihydroperoxides can generate singlet oxygen as the active oxidant 8,10 in olefin oxidation, for example.…”

“…The ability of gem-dihydroperoxides to generate radicals allows them to be furthermore exploited as radical initiators, [2][3][4][5] for example methyl ethyl ketone peroxide is used in the manufacturing of acrylic resins, reinforced plastics, and unsaturated polyester resins. 6 Itoh and co-workers established two catalyst-free preparative protocols for gem-dihydroperoxides, of which the one employs hydrogen peroxide 12 as terminal oxidant and the other molecular oxygen.…”