Synthesis and X-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]undecanes

Miura, Masahiro; Ikegami, Akio; Nojima, Màsatomo; Kusabayashi, Shigekazu; McCullough, Kevin J.; Walkinshaw, Malcolm D.

doi:10.1039/p19830001657

Cited by 5 publications

(1 citation statement)

References 5 publications

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“…Most of known symmetrical tetraoxanes were synthesized by the acid-catalyzed cyclocondensation of hydrogen peroxide with ketones or benzaldehydes; ,,,− the trimethylsilyl trifluoromethanesulfonate (TMSOTf)-catalyzed cyclocondensation of bis(trimethylsilyl) peroxides with carbonyl compounds; , the ozonolysis of olefins, , enol ethers, and O-alkyl oximes; − the BF 3 -catalyzed rearrangement of dioxetanes; and the rearrangement of ozonides in the presence of catalytic amounts of SbC1 5 or ClSO 3 H …”

Section: Introductionmentioning

confidence: 99%

Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones

et al. 2009

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A facile, experimentally simple, and selective method was developed for the synthesis of bridged 1,2,4,5-tetraoxanes based on the reaction of hydrogen peroxide with beta-diketones catalyzed by strong acids (H(2)SO(4), HClO(4), HBF(4), or BF(3)). The yields of the target products vary from 44% to 77%. 1,2,4,5-Tetraoxanes can easily be separated from other reaction products by column chromatography. A high concentration of a strong acid is a key factor determining the selectivity of formation and the yield of 1,2,4,5-tetraoxanes. Unlike many compounds containing the O-O bond, which undergo rearrangements in acidic media, the resulting cyclic peroxides are quite stable under these conditions.

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Section: Introductionmentioning

confidence: 99%

Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones

et al. 2009

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Analytical and Safety Aspects of Organic Peroxides and Related Functional Groups

Zabicky

2009

Patai's Chemistry of Functional Groups

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Introduction Hydrogen Peroxide Oxidation Indices Hydroperoxides Peroxyacids and their Functional Derivatives Dialkyl Peroxides Ozonides Miscellaneous Functions Bearing the O  O Group Safety Issues Acknowledgments

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ChemInform Abstract: SYNTHESIS AND X‐RAY ANALYSIS OF 2,3,5,6,11‐PENTAOXABICYCLO(5.3.1)UNDECANES

Miura¹,

Ikegami²,

Nojima³

et al. 1983

Chemischer Informationsdienst

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Synthesis and X-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]undecanes

Cited by 5 publications

References 5 publications

Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones

Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones

Analytical and Safety Aspects of Organic Peroxides and Related Functional Groups

ChemInform Abstract: SYNTHESIS AND X‐RAY ANALYSIS OF 2,3,5,6,11‐PENTAOXABICYCLO(5.3.1)UNDECANES

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