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Cited by 26 publications
(12 citation statements)
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“…In continuation of our previous reports on the synthesis [31][32][33][34], and applications of dihydroperoxides as versatile and potent oxidants for various transformations [35][36][37][38][39][40][41], we were encouraged to investigate the hitherto unexplored oxidative potential of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane (DHPDMDO) in thiocyanation of aromatic and heteroaromatic compounds. Herein, we wish to report, for the first time, the convenient application of trans-3,5dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxidant for in situ generation of thiocyanate ion (SCN + ) from sodium thiocyanate which undergoes regioselective electrophilic substitution with anilines 1a-p and indoles 1q-v to produce the respective thiocyanate derivatives 2 in high to excellent yields (Table 2, Scheme 2).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…In continuation of our previous reports on the synthesis [31][32][33][34], and applications of dihydroperoxides as versatile and potent oxidants for various transformations [35][36][37][38][39][40][41], we were encouraged to investigate the hitherto unexplored oxidative potential of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane (DHPDMDO) in thiocyanation of aromatic and heteroaromatic compounds. Herein, we wish to report, for the first time, the convenient application of trans-3,5dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxidant for in situ generation of thiocyanate ion (SCN + ) from sodium thiocyanate which undergoes regioselective electrophilic substitution with anilines 1a-p and indoles 1q-v to produce the respective thiocyanate derivatives 2 in high to excellent yields (Table 2, Scheme 2).…”
Section: Resultsmentioning
confidence: 99%
“…Recently, gem-dihydroperoxides have received considerable interest as high potent oxidants for various organic transformations [23][24][25][26][27][28][29][30]. Following our ongoing research on the synthesis of gem-dihydroperoxides [31][32][33][34], and their applications in a variety of organic conversions including oxidation of alcohols to ketones [35], selective sulfoxidation of sufides [36], selective halogenation of aromatic compounds [37], epoxidation of α,β-unsaturated ketones [38], oxidative conversion of aldehydes, amines, alcohols and halides to nitriles [39], ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives [40], and synthesis of benzimidazoles and benzothiazoles [41], herein, we were encouraged to study the oxidative potential of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane (DHPDMDO) for thiocyanation of anilines and their related heterocyclic compounds such as indoles.…”
Section: Introductionmentioning
confidence: 99%
“…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). So, in continuation of our interest in the application of DHPDMDOs, we used DHPDMDOs for in situ generation of Br + from NH 4 Br for catalysis of oxidative aromatization of 1,4-dihydropyridines to corresponding pyridines under mild conditions and short reaction times (Scheme 2).…”
Section: Public Interest Statementmentioning
confidence: 99%
“…Also, these compounds are important intermediates in synthesis of a number of classes of peroxides including tetraoxanes [4][5][6], silateraoxans [7], spirobisperoxyketals [8,9], bisperoxyketals [10], and 1,2,4,5-tetraoxacycloalkanes [11,12]. Gem-dihydroperoxides have also been employed as initiators for radical polymerization reactions [13], as precursors for synthesis of dicarboxylic acid esters [14], and as reagents for oxidation reactions such epoxidation of α,β-unsaturated ketones [15,16], enantioselective oxidation of 2-substituted 1,4-naphtoquinones [17], oxidation of sulfides [18,19], and as suitable oxidants in other synthetic organic reactions [15,20,21]. Three major methods reported for the synthesis of gem-dihydroperoxides are: (i) ozonolysis of ketone enol ethers or α-olefines in the presence of aqueous H 2 O 2 [11, Caution: Although we did not encounter any problem with gem-dihydroperoxides, peroxides are potentially explosive and should be handled with precautions; all reactions should be carried out behind a safety shield inside a fume hood and heating should be avoided Table 1.…”
Section: Introductionmentioning
confidence: 99%