Convenient Synthesis of Geminal Bishydroperoxides by the Reaction of Ketones with Hydrogen Peroxide

Terent’ev, Alexander O.; Platonov, M.M.; Ogibin, Yu. N.; Nikishin, G. I.

doi:10.1080/00397910701226384

Cited by 73 publications

(47 citation statements)

References 14 publications

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“…[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.…”

Section: Introductionmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

“…4,5,8,16,17 Brønsted acids are comparably active as either homogeneous (sulfuric acid 3 ) or heterogeneous catalysts, for example silica-sulfuric acid 2 or triflicacid-functionalized silica-coated ferromagnetic nanoparticles.…”

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confidence: 99%

“…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.…”

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confidence: 99%

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gem-Bishydroperoxides

Tonder¹

2014

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research spotlight gem-Bishydroperoxides Compiled by Johannes H. van Tonder Johannes grew up in the diamond city Kimberley, South Africa. He pursued his interest in science by obtaining a B.Sc. degree in chemistry and biology in 2004 from the University of the Free State. His fondness for organic chemistry led him to procure a M.Sc. degree from the same institution in 2008. He is currently completing a Ph.D. degree under the supervision of Professor B. C. B. Bezuidenhoudt at the University of the Free State.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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gem-Bishydroperoxides

Tonder¹

2014

Synlett

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“…The Sm(NO3)3·6H2O catalyst was chosen due to its successful use in our previous work to catalyze the cyclocondensation of NНacids with formaldehyde and α,ω-diols or α,ω-dithiols to afford 1,5,3-dioxazepanes 14 or 1,5,3-dithiazacycloalkanes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pentaoxaspiroalkanes and pentaoxocanes catalyzed by lanthanide compounds

Makhmudiyarova¹,

Khatmullina²,

Rakhimov³

et al. 2016

Arkivoc

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1,1‐Dihydroperoxides

Schwartz

Dussault

2014

Patai's Chemistry of Functional Groups

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Gem ‐dihydroperoxides ( g ‐DHPs), often referred to as 1,1‐dihydroperoxides, are a class of molecules of interest because of their reactivity as well as their utility as synthetic reagents and intermediates. This review begins with a listing of previous reviews and commercially available g ‐DHPs, followed by a brief discussion of safety and regulatory issues. The properties of g ‐DHPs are then overviewed, with an emphasis on the physical properties, biological activity, thermal stability, spectroscopic properties, and behavior on chromatographic media. The remaining sections describe the synthesis and reactions of g ‐DHPS. The largest of these sections describes the various methods for synthesis of g ‐DHPs based upon class of catalyst or reagent and compares applications of different reagents selected target skeletons. One of the most significant applications of g ‐DHPs, their use as precursors for 1,2,4,5‐tetraoxanes, is discussed in detail, including tabular comparisons of approaches to selected skeletons. The chapter concludes with a discussion of other important reactions of g ‐DHPs, including alkylations, nucleophilic and electrophile‐promoted additions to alkenes, acetalizations, acylations and acylation‐promoted fragmentations, acid‐promoted dimerizations and decompositions, silylations, and application as oxygen transfer agents.

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Convenient Synthesis of Geminal Bishydroperoxides by the Reaction of Ketones with Hydrogen Peroxide

Cited by 73 publications

References 14 publications

gem-Bishydroperoxides

gem-Bishydroperoxides

Synthesis of pentaoxaspiroalkanes and pentaoxocanes catalyzed by lanthanide compounds

1,1‐Dihydroperoxides

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