Über Peroxyde der Äther, der Carbonyl‐Verbindungen und die Ozonide

Rieche, Alfred

doi:10.1002/ange.19580700902

Cited by 82 publications

(39 citation statements)

References 111 publications

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“…[2c] Although the formation of the hydroxy-hydroperoxide,M e 2 C(OH)(OOH), from acetone and HOOH is well established in the peroxide chemistry, [13] our MTOcatalyzed addition of HOOOH to acetone is the first example Scheme 2. Ozonation of dimethylphenylsilane-derivatized polystyrene bead 2,and further efficient catalytic release of hydrogen trioxide from the polymer 3.…”

Section: Angewandte Chemiementioning

confidence: 99%

A Simple and Efficient Preparation of High‐Purity Hydrogen Trioxide (HOOOH)

Strle

Cerkovnik

2015

Angewandte Chemie

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Asimple and efficient method allows the synthesis of solutions of high-purity hydrogen trioxide (HOOOH), released in the low-temperature methytrioxorhenium(VII) (MTO)-catalyzed transformation of the ozonized polystyrene-supported dimethylphenylsilane.H igh-purity hydrogen trioxide solutions in diethyl ether,separated from the polymer and free of any reactants and by-products,c an be stored at À20 8 8Cfor weeks.Byremoving the solvent in vacuo,HOOOH could be isolated in highly pure form or transferred to other solvents,t hus significantly extending the researchp erspectives of HOOOH for novel applications.

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Section: Angewandte Chemiementioning

confidence: 99%

A Simple and Efficient Preparation of High‐Purity Hydrogen Trioxide (HOOOH)

Strle

Cerkovnik

2015

Angewandte Chemie

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“…Furthermore, treatment of 4-hydroxybutyrophenone with 30 % hydrogen peroxide generated the hydroperoxide (2) and, on aging, peroxide (1). Hydroperoxides similar to (2) have been reported to form peroxides readily (14,15).…”

Section: Introductionmentioning

confidence: 99%

Acid-catalyzed rearrangement of hydroperoxides. II. Phenylcycloalkyl hydroperoxides

Anderson¹,

Smith²

1968

Can. J. Chem.

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The acid-catalyzed rearrangement of 1-phenylcycloalkyl hydroperoxides has been investigated using the cyclohexyl, cyclopentyl, and cyclobutyl compounds. Evidence was sought for rearrangement of the cycloalkyl group in competition with migration of thephenyl group during the reaction. Such a rearrangement would result in ring expansion of the cycloalkyl group to give, ultimately, products formed by cycloalkyl ring opening.No evidence for such a reaction was found in the case of 1-phenylcyclohexyl hydroperoxide; only the expected products, phenol and cyclohexanone, were detected. However, rearrangement of l-phenylcyclopentyl hydroperoxide gave, besides the expected phenol and cyclopentanone, significant amounts of the ring-opened compound 4-hydroxyvalerophenone as its acetate. A second product, 1-phenylcyclopentene, arose by elimination of hydrogen peroxide from the hydroperoxide.1-Phenylcyclobutyl hydroperoxide proved to undergo ring expansion with great facility. Only the ring expanded products, 2-phenyl-2-tetrahydrofuryl hydroperoxide and its corresponding peroxide, could be isolated in the treatment of 1-phenylcyclobutanol with hydrogen peroxide using catalytic amounts of mineral acids. However, in the absence of catalysts, 1-phenylcyclobutyl hydroperoxide was formed in detectable amounts and its presence was demonstrated by decomposition with ferrous sulfate to butyrophenone and 1,6-dibenzoylhexane.It seems reasonable that ring strain is the factor promoting the ring expansion of 1-phenylcyclobutyl hydroperoxide. In the case of 1-phenylcyclopentyl hydroperoxide, it is suggested that the steric interaction of the ortho hydrogens of the phenyl group with the cyclopentyl ring protons has the effect of slowing the migration of the phenyl group sufficiently that alkyl migration can occur to give the observed ringopened products.

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“…[4,5] Auch in der Atmosphäre spielen Peroxide eine wesentliche Rolle,z .B.b eim Abbau der Ozonschicht. [3,4] Die Spaltung einer Peroxidbindung in unverdünnten Alkylperoxiden, die nur eine verhältnismäßig geringe thermische Energie erfordert oder leicht katalytisch eingeleitet werden kann, initiiert häufig sehr exotherme Zerfallsreaktionen, die zu Explosionen oder sogar Detonationen führen kçnnen. 14 8 8C) bildet sich in der Stratosphäre bei der Oxidation von Methan.…”

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“…14 8 8C) bildet sich in der Stratosphäre bei der Oxidation von Methan. [7] Wiev on Rieche bereits vor 60 Jahren beobachtet, wird die Empfindlichkeit von Alkylperoxiden durch große organische Substituenten herabgesetzt, [3] dabei wird das Temperament von Peroxiden mit verschieden großen organischen Substituenten vom grçßeren bestimmt. [3,4] Die Spaltung einer Peroxidbindung in unverdünnten Alkylperoxiden, die nur eine verhältnismäßig geringe thermische Energie erfordert oder leicht katalytisch eingeleitet werden kann, initiiert häufig sehr exotherme Zerfallsreaktionen, die zu Explosionen oder sogar Detonationen führen kçnnen.…”

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Keine Scheu vor perfluorierten Peroxiden: Synthese und Strukturen von überraschend inerten Perfluoralkylperoxiden

Nissen¹,

Stüker²,

Drews³

et al. 2019

Angewandte Chemie

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Wirb erichten über die Festkçrperstrukturen von Bis(nonafluor-tert-butyl)peroxid [(F 3 C) 3 CO] 2 und Bis(undecafluor-2-methyl-2-butyl)peroxid [(C 2 F 5 )(F 3 C) 2 CO] 2 .D iese Peroxide wurden über die Reaktion des jeweiligen Hypofluorits mit fluorierter Silberwolle dargestellt. Ihre nach In-situ-Kristallisation erhaltenen Strukturen weisen aufgrund der sterischa nspruchsvollen Perfluoralkylgruppen ungewçhnliche COOC-Diederwinkel von 1808 8,s owie verlängerte O-O-Abstände auf.D ie perfluorierten Alkylperoxides ind weder schock-(> 40 J) nochr eibungsempfindlich( > 360 N). Darüber hinaus reagieren sie nicht mit Halogensäuren (HX, X = F, Cl, Br,I)oder elementaren Halogenen (X 2 ). Ferrocen wird von [(F 3 C) 3 CO] 2 zu [Fe III Cp 2 ][OC(CF 3 ) 3 ]o xidiert.

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Über Peroxyde der Äther, der Carbonyl‐Verbindungen und die Ozonide

Abstract: Erweiterte Fassung eines Plenai--Vortrages am 4. Oktober 1957 auf der GDCh-Hauptversammlung in BerlinDas Gebiet der Peroxyde, welches bereits seit dreißig Jahren intensiv bearbeitet wird, gewinnt steigend an Interesse.

Cited by 82 publications

References 111 publications

A Simple and Efficient Preparation of High‐Purity Hydrogen Trioxide (HOOOH)

A Simple and Efficient Preparation of High‐Purity Hydrogen Trioxide (HOOOH)

Acid-catalyzed rearrangement of hydroperoxides. II. Phenylcycloalkyl hydroperoxides

Keine Scheu vor perfluorierten Peroxiden: Synthese und Strukturen von überraschend inerten Perfluoralkylperoxiden

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