Synthesis of gem-dihydroperoxides from ketones using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst

Mild and Efficient Strontium Chloride Hexahydrate-Catalyzed Conversion of Ketones and Aldehydes into Corresponding gem- Dihydroperoxides by Aqueous H2O2

“…Most of the documented protocols for the synthesis of gem -dihydroperoxides in the literature suffer from significant drawbacks such as the use of strong acidic media, concentrated H 2 O 2 and low yields [ 1 ]. These methods mainly utilize a Brönsted or Lewis acid e.g., HCO 2 H [ 12 , 20 , 36 ], NaHSO 4 -SiO 2 [ 37 ], H 2 SO 4 [ 38 ], F 3 CCO 2 H [ 39 ], H 2 WO 4 [ 29 , 38 ], and BF 3 ·OEt 2 [ 30 , 39 ] to promote the conversion of ketones, ketals or enol ethers into the corresponding DHPs on treatment with aqueous H 2 O 2 . Other catalysts such as methyltrioxorhenium (prepared from Re 2 O 7 ) [ 2 ], ceric ammonium nitrate (CAN) [ 32 ], and iodine [ 33 ] have also been reported to promote such transformations.…”

Mild oxidative aromatization of 1,4-dihydropyridines with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane promoted by ammonium bromide/HOAc in water/MeCN

“…Thus, as regards the importance of pyridines, the development of a simple, efficient, mild, and versatile method for the oxidation of 1,4-DHP is of interest in organic methodology. Recently, gem-dihydroperoxides have been synthesized and have been used for oxidation reactions Bunge, Hamann, McCalmont, & Liebscher, 2009;Das, Krishnaiah, Veeranjaneyulu, & Ravikanth, 2007;Das, Veeranjaneyulu, Krishnaiah, & Balasubramanyam, 2008;Ghorai & Dussault, 2008;Li, Hao, Zhang, & Wu, 2009;Žmitek, Zupan, Stavber, & Iskra, 2006;Žmitek, Zupan, Stavber, & Iskra, 2007). We have synthesized trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane (Scheme 1) and used it as a powerful oxidant in some organic reactions (Azarifar & Khosravi, 2010a;Azarifar & Khosravi, 2010b;Azarifar, Khosravi, & Soleimanei, 2009;Azarifar, Najminejad, & Khosravi, 2013;Khosravi, 2014;Khosravi, 2015;Khosravi & Kazemi, 2012;Khosravi, Mobinikhaledi, Kazemi, Azarifar, & Rahmani, 2014;Khosravi, Pirbodaghi, Kazemi, & Asghari, 2015).…”

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

“…Isoxazoles and pyrazoles are also in demand because of their importance both as synthetic intermediates [10] and as pharmacological agents [11]. Isoxazoles and 2-pyrazoles can be easily obtained by oxidation of isoxazolines [12][13][14][15][16][17] and 2-pyrazolines [18], respectively. Several methods have been reported for oxidation of isoxazolines and 2-pyrazolines including Pd-C-acetic acid [19], carbon-activated oxygen [20], cobalt soap of fatty acids [21] [23], manganese dioxide [24], potassium permanganate [24,25], silver nitrate [26], iodobenzene diacetate [27], zirconium nitrate [28], nickel peroxide [29], chromite [16], N-bromosuccinimide (NBS) [30], manganese triacetate [31], sodium bicarbonate-dimethylformamide [32], 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) [33], sodium carbonate-methanol [10], and tetrakis pyridine nickel(II) dichromate [34].…”

“…Recently, gem-dihydroperoxides have been synthesized and have been of interest as new and effective oxidants in organic synthesis [17,[35][36][37][38][39][40][41]. 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].…”