A Simple Laboratory Method for the Preparation of (Dimeric) Ketone Peroxides.

Ledaal, Tore; Solbjör, T.; Thom, Erling; Stoll, E.; Eriksson, G.; Blinc, R.; Paušak, S.; Ehrenberg, L.; Dumanović, J.

doi:10.3891/acta.chem.scand.21-1656

Cited by 12 publications

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“…For example, reaction of cyclohexanone and hydrogen peroxide in acetic acid above 60°is variously reported to give cyclohexanone diperoxide (IV) (14-23% yield) or a mixture of cyclohexanone diperoxide (IV) (4%) and triperoxide (I) (10%) (Kharasch and Sosnovsky, 1958;Story et al, 1970) whereas at room temperature a good yield (72%) of triperoxide (I) was obtained (Story et al, 1970). By carrying out the reaction at room temperature in acetonitrile using perchloric acid catalyst, the product has been variously reported as l-hydroxy-l'-hydroperoxydicyclohexylperoxide (V) (53% yield) (Ledaal, 1967;Story et al, 1970), or cyclohexanone triperoxide (I) (83%) when a longer reaction time was used (Story et al, 1970).…”

Section: Introductionmentioning

confidence: 99%

“…OH HOO >o 0-0 V 1-Hydroxy-T-hydroperoxydicyclohexylperoxide (V) itself, under acid catalysis, is converted slowly to diperoxide (IV) on standing at room temperature, but at 6°is converted to essentially pure triperoxide (I) (Story et al, 1970). Ledaal reported that the same reaction at 0°C gave cyclohexanone diperoxide (IV) (Ledaal, 1967).…”

Section: Introductionmentioning

confidence: 99%

“…The solvents first investigated were acetic acid and acetonitrile because they are miscible with both cyclohexanone and aqueous hydrogen peroxide, and they have been used for cyclic peroxide preparation in earlier work (Criegee et al, 1949; Kharasch and Sosnovsky, 1958; Ledaal, 1967;Story et al, 1970). A practical method of preparing hexadecanolide from cyclohexanone triperoxide is described.…”

Section: Introductionmentioning

confidence: 99%

“…Comparison of Acid Catalysts. Perchloric acid is the only acid that has been used for the one-step synthesis of cyclohexanone triperoxide (I) from cyclohexanone (Kharasch and Sosnovsky, 1958; Ledaal, 1967;Story et al, 1968Story et al, , 1970. Hydrochloric acid gave a 52% yield of triperoxide (I) in a two-step procedure (Criegee et al, 1949) and sulfuric acid has been used as a catalyst for cyclohexanone diperoxide (IV) preparation (Stoll and Scherrer, 1930;Dilthey et al, 1940).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Hexadecanolide

Harding¹,

Whalen²

1975

Product R&D

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Hexadecanolide

Harding¹,

Whalen²

1975

Product R&D

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“…Kao što je navedeno u prethodnom delu, 3,6-substituisani derivati 1,2,4,5-tetraoksacikloheksana (1,2,4,5-tetraoksani) poznati su već dugi niz godina i korišćeni su u različite svrhe (51)(52)(53)(54)(55)(56). Lako se dobijaju kiselo-katalizovanom reakcijom peroksiacetalizacije karbonilnih jedinjenja vodonik-peroksidom ili pomoću bistrimetilsililperoksida u prisustvu TMSOTf (48,57,58).…”

Section: Tetraoksani -1245-tetraoksacikloalkaniunclassified

Antitumor effect of steroidal tetraoxanes on malignantly transformed human cell lines

Žižak¹

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Za CiuANTITUMORSKI EFEKAT STEROIDNIH TETRAOKSANA NA MALIGNO TRANSFORMISANE ĆELIJSKE LINIJEČOVEKA REZIME Uvod: Pronalaženje agenasa sa potencijalnim antitumorskim dejstvom je imperativ u modernoj onkologiji. Pri tome se sve više zapaža da određene hemijske strukture imaju specifičnije toksično dejstvo na maligne ćelije. Otkriće artemizinina je označilo početak istraživanja peroksida kao potencijalne zamene za tradicionalne antimalarijske lekove, a iz ovih istraživanja nastala je i strukturno jednostavna klasa peroksida -1,2,4,5-tetraoksani, za koje je ubrzo pokazano da pored antimalarijskog pokazuju i snažan antiproliferativni efekat. Maligne ćelije imaju poremećaje u regulatornim mehanizmima koji upravljaju ćelijskom proliferacijom i homeostazom. Sposobnost tumorskih ćelijskih populacija da povećaju broj ćelija je određena ne samo intenzitetom ćelijske proliferacije, već i brzinom uklanjanja ćelija. Programirana ćelijska smrt -apoptoza, predstavlja glavni izvor ovog uklanjanja.Cilj rada je bio da se odredi nivo citotoksičnog dejstva grupe mešovitih tetraoksana prema različitim humanim malignim ćelijama, kao i da se odredi koeficijenat selektivnosti u njihovom dejstvu u odnosu na zdrave imunokompetentne ćelije. U cilju dobijanja uvida u mehanizam dejstva ispitivanih jedinjenja odrediće se tip ćelijske smrti koju indukuju ispitivani tetraoksani, kao i produkcija reaktivnih kiseoničnih vrsta u Hela ćelijama. Cilj 3D QSAR studije o antiproliferativoj aktivnosti trideset tri 1,2,4,5-tetraoksanska derivata prema Hela i Fem-x tumorskim ćelijskim linijama, je bio da se utvrdi koje su najvažnije farmakofore steroidnih tetraoksana koje utiču na potenciju ispitivanih jedinjenja prema HeLa i Fem-x tumorskim ćelijskim linijama. Materijal i metode:Citotoksično dejstvo tetraoksana DO-122 -DO-124 i DO-126 -DO-128, prema pet tumorskih ćelijskih linija je ispitivano standardnim MTT testom. U cilju određivanja tipa ćelijske smrti indukovane tretmanom ispitivanim tetraoksanima načinjena je morfološka analiza HeLa ćelija obojenih smešom akridin oranža i etidijum bromida. Analiza određivanja distribucije faza ćelijskog ciklusa HeLa ćelija obojenih propidijum jodidom, urađena je na protočnom citometru. Produkcija intraćelijskih reaktivnih vrsta kiseonika (ROS) je merena fluorometrijski pomoću fluorescentne boje 2',7'-dihlorodihidrofluorescein diacetata. Zavisnost strukture i funkcije trideset tri 1,2,4,5-tetraoksanskih derivata prema HeLa i Fem-x ćelijskim linijama pokazana je 3D QSAR studijom. Rezultati:Ispitivani tetraoksani pokazuju dozno-zavisnu antiproliferativnu aktivnost u mikromolarnim koncentracijama prema ciljnim tumorskim ćelijama, uz dobru selektivnost u aktivnosti prema tumorskim ćelijama, u odnosu na normalne imunokompetentne ćelije. 24-časovni tretman HeLa ćelija sa svim ispitivanim tetraoksanima indukuju tipične morfološke karakteristike kasne apoptoze (kondenzovana i/ili fragmentisana jedra). Posle 24 i 48 časova inkubacije sa tetraoksanima, broj HeLa ćelija u G1 fazi se značajno uvećava. Nakon tretmana HeLa ćelija is...

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Peroxy Compounds, Organic

Klenk

Götz

Siegmeier

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Alkyl Hydroperoxides 2.1. Properties 2.2. Production 2.3. Uses 3. Dialkyl Peroxides 3.1. Properties 3.2. Production 3.3. Uses 4. Peroxycarboxylic Acids 4.1. Properties 4.2. Production 4.2.1. Peroxycarboxylic Acids from Carboxylic Acids and Hydrogen Peroxide 4.2.2. Peroxycarboxylic Acids from Carboxylic Anhydrides and Hydrogen Peroxide 4.2.3. Peroxycarboxylic Acids from Carboxylic Acid Chlorides and Hydrogen Peroxide 4.2.4. Peroxycarboxylic Acids by Autoxidation of Aldehydes 4.3. Uses 5. Diacyl Peroxides 5.1. Properties 5.2. Production 5.3. Uses 6. Peroxycarboxylic Esters 6.1. Properties 6.2. Production 6.3. Uses 7. α‐Oxyperoxides 7.1. Properties 7.2. Production 7.3. Uses 8. α‐Aminoperoxides 8.1. Properties 8.2. Production 8.3. Uses 9. Safety Measures 9.1. Hazards 9.2. Transportation and Storage 9.3. Handling 10. Toxicology

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A Simple Laboratory Method for the Preparation of (Dimeric) Ketone Peroxides.

Cited by 12 publications

References 0 publications

Synthesis of Hexadecanolide

Synthesis of Hexadecanolide

Antitumor effect of steroidal tetraoxanes on malignantly transformed human cell lines

Peroxy Compounds, Organic

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