α-Substituted organic peroxides: synthetic strategies for a biologically important class of gem-dihydroperoxide and perketal derivatives

Žmitek, Katja; Zupan, Marko; Iskra, Jernej

doi:10.1039/b711647k

Cited by 86 publications

(43 citation statements)

References 126 publications

(92 reference statements)

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“…IR spectra were recorded on a Perkin Elmer GX FT IR spectrometer from KBr pellets. 1 H and 13 C NMR spectra were measured for samples in CDCl 3 with a JEOL FX 90Q instrument at 90 and 22.5 MHz respectively, using Me 4 Si as internal standard. Melting points were measured on a SMPI apparatus.…”

Section: Methodsmentioning

confidence: 99%

“…Gem-dihydroperoxides are stable derivatives of ketones and aldehydes, 1 have been remarkable compounds because of their relevance to peroxidic anti malarial drugs. 2 Also, these compounds are important intermediates in the synthesis of a number of classes of peroxides including tetraoxanes, 3 silateraoxans, 4 spirobisperoxyketals, 5 bisperoxyketals, 6 1,2,4,5-tetraoxa cycloalkanes.…”

Section: Introductionmentioning

confidence: 99%

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Zinc Chloride Anhydrous as New and Effective Catalyst for Conversion of Ketones and Aldehydes to Corresponding Gem‐dihydroperoxides

Khosravi

Kazemi

2012

J Chinese Chemical Soc

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Zinc Chloride Anhydrous as New and Effective Catalyst for Conversion of Ketones and Aldehydes to Corresponding Gem‐dihydroperoxides

Khosravi

Kazemi

2012

J Chinese Chemical Soc

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“…Several approaches to the synthesis of peroxide-containing substrates have been established over the years. 3 Schenck introduced the preparation of hydroperoxides in 1948 by the radical addition of singlet oxygen to alkenes. 4,5 Kharasch discovered that transition metals could be employed in the synthesis of hydroperoxides from alkenes, ketones and amines.…”

Section: Introductionmentioning

confidence: 99%

Advances in the synthesis of acyclic peroxides

et al. 2017

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Peroxide-containing compounds are an attractive synthetic target, given their widespread abundance in nature, with many displaying potent antimalarial and antimicrobial properties. This review summarises the many developments in the synthesis of acyclic peroxides, with a particular focus on the past 20 years, and seeks to update organic chemists about these new approaches. The synthetic methodologies have been subdivided into metal-catalysed reactions, organocatalytic reactions, direct oxidation reactions, miscellaneous reactions and enzymatic routes to acyclic peroxides

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“…Gem-dihydroperoxides (DHPs) are considered as stable derivatives of ketones and aldehydes [1], which have been of considerable interest because of their relevance to peroxidic antimalarial drugs [2,3]. 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].…”

Section: Introductionmentioning

confidence: 99%

Sulfamic acid: as a green and reusable homogeneous catalyst for peroxidation of ketones and aldehydes using aqueous 30 % H2O2

et al. 2015

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22, 23], (ii) reaction of ketals with H 2 O 2 in the presence of tungstic acid [24], or BF 3 ·Et 2 O [25], and (iv) peroxidation of ketones using an acidic solvent [26]. However, many of these methods have certain drawbacks including use of concentrated H 2 O 2 and excess acid, low yield, limited substrate range and production of mixtures of peroxidic products [27]. Also, poor selectivity and the presence of ozonesensitive groups in the substrates are further limitations in ozonolysis reaction. To avoid such limitations, recently, reactions of ketones and aldehydes with H 2 O 2 in the presence of Lewis acids in organic solvents have been reported. Among the Lewis acids, I 2 [28, 29], ceric ammonium nitrate (CAN) [30], CSA [31], NaHSO 4 ·SiO 2 [32], Re 2 O 7 [33], and PMA [34] have been reported as the catalysts in the synthesis of gem-dihydroperoxides with aqueous H 2 O 2 .In continuation of our efforts to explore new catalysts for synthesis of gem-dihydroperoxides [35,36]. Herein, we wish to introduce the sulfamic acid as a low-cost, green and effective recoverable solid catalyst in the synthesis of gemdihydroperoxides from ketones and aldehydes with 30 % aqueous H 2 O 2 at room temperature (Scheme 1).Sulfamic acid (SA) (NH 2 SO 3 H) is commercially available green heterogeneous catalyst that is solvable in water and has been used widely as an effective catalyst in organic synthesis [37,38]. ExperimentalSolvents, reagents, and chemical materials were obtained from Aldrich and Merck chemical companies and purified prior to use. Nuclear magnetic resonance spectra were recorded on JEOL FX 90Q using tetramethylsilane (TMS) as an internal standard. Infrared spectra were recorded on a PerkinElmer GX FT IR spectrometer (KBr pellets).Abstract Sulfamic acid has been used as an active, lowcost and reusable solid catalyst for conversion of ketones and aldehydes to corresponding gem-dihydroperoxides using 30 % aqueous hydrogen peroxide at room temperature. The reactions proceed with high rates and excellent yields.

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α-Substituted organic peroxides: synthetic strategies for a biologically important class of gem-dihydroperoxide and perketal derivatives

Cited by 86 publications

References 126 publications

Zinc Chloride Anhydrous as New and Effective Catalyst for Conversion of Ketones and Aldehydes to Corresponding Gem‐dihydroperoxides

Zinc Chloride Anhydrous as New and Effective Catalyst for Conversion of Ketones and Aldehydes to Corresponding Gem‐dihydroperoxides

Advances in the synthesis of acyclic peroxides

Sulfamic acid: as a green and reusable homogeneous catalyst for peroxidation of ketones and aldehydes using aqueous 30 % H2O2

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