Osmium and Ruthenium Tetroxide-Catalyzed Oxidations of Pyrene<sup>1</sup>

Oberender, Frederick; Dixon, Joseph A.

doi:10.1021/jo01091a016

Cited by 50 publications

(16 citation statements)

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“…The selective RuO 4 ‐catalyzed oxidation of pyrene at its 4‐ and 5‐positions is the starting point for the synthesis route and gives the dione 1 . This one‐step reaction was reported by Harris and co‐workers in 2005 as an alternative to the toxic OsO 4 ‐catalyzed oxidation of pyrene . In this regard, RuO 4 is generated in situ from RuCl 3 ⋅3 H 2 O and NaIO 4 , and the oxidation takes place in a solvent mixture of MeCN, CH 2 Cl 2 and H 2 O (1:1:1.25).…”

Section: Resultsmentioning

confidence: 68%

“…This one-step reaction was reported by Harris and co-workers in 2005 as an alternative to the toxic OsO 4 -catalyzed oxidation of pyrene. [47,48] In this regard, RuO 4 is generated in situ from RuCl 3 ·3 H 2 O and NaIO 4 , and the oxida-tion takes place in a solvent mixture of MeCN, CH 2 Cl 2 and H 2 O (1:1:1.25). In 1981, Sharpless and co-workers reported that addition of MeCN to the RuO 4 -catalyzed oxidation greatly improves the effectiveness of the reaction.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

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Synthesis, Photophysical and Electronic Properties of New Red‐to‐NIR Emitting Donor–Acceptor Pyrene Derivatives

Merz

Dietz

Vonhausen

et al. 2019

Chemistry A European J

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We synthesized new pyrene derivatives with strong bis(para‐methoxyphenyl)amine donors at the 2,7‐positions and n‐azaacene acceptors at the K‐region of pyrene. The compounds possess a strong intramolecular charge transfer, leading to unusual properties such as emission in the red to NIR region (700 nm), which has not been reported before for monomeric pyrenes. Detailed photophysical studies reveal very long intrinsic lifetimes of >100 ns for the new compounds, which is typical for 2,7‐substituted pyrenes but not for K‐region substituted pyrenes. The incorporation of strong donors and acceptors leads to very low reduction and oxidation potentials, and spectroelectrochemical studies show that the compounds are on the borderline between localized Robin‐Day class‐II and delocalized Robin‐Day class‐III species.

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Section: Resultsmentioning

confidence: 68%

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

Synthesis, Photophysical and Electronic Properties of New Red‐to‐NIR Emitting Donor–Acceptor Pyrene Derivatives

Merz

Dietz

Vonhausen

et al. 2019

Chemistry A European J

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“…The lactol is very similar to the fluorescein-like lactone. The presence of such a lactol is supported by the following data: Oxidation of pyrene (5) with ozone in glacial acetic acid [31] or with H202 and Os04 [32] gives 4-formylphenanthrene-5-carboxylic acid (7) which normally exists as the lactol (6) [33,34]. Compound (6) or Ketocarboxylic acids whose functional groups are at the peri positions of a condensed ring system behave in a similar manner to formylcarboxylic acids [34J.…”

Section: Possible Structures Of Carbon Surface Oxidesmentioning

confidence: 99%

Surface Oxides of Carbon

Boehm

Diehl

Heck

et al. 1964

Angew. Chem. Int. Ed. Engl.

527

260

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On oxidation of graphitic carbon, acidic surface oxides (or hydroxides in the presence of water) are formed at the boundaries of the carbon layers. It was found that the reaction of oxygen with microcrystalline carbon at 400-450 "C yields four groups of diflerent acidities. One strongly acidic group and one weakly acidic carboxyl group have been detected, as well us a phenolic hydroxyl group; a carbonyl group is probably also present. With dissolved oxidizing agents, one equiialent of another strongly acidic carboxyl group is formed in addition at room temperature. The possible constitutions o f the acidic surface oxides are discussed. Chemically detectable surface oxides are also formed on the surfarc. of diamond. In the presence of oxygen at 800-900 "C under reduced pressure, diamond is transformed into black carbon. Surface oxides play a par[ in this transjbrmation.

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“…Sodium metaperiodate has, however, been used conjointly with s uc h diol-formin g agents as osmium tetraoxid e or ruth e nium te traoxid e [42]. The present s tud y s hows that , wh e n it reacts with certain polycycli c, aromatic co mpound s, periodi c acid ha s the ability to (1) produ ce radi cals by abstraction of (a) elec tron s or (b) proton s, (2) oxidize a me thin e gro up at an activa ted doubl e bond of polycycli c, aromatic compound s, or (3) oxidize an activated met hyl e ne group.…”

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confidence: 99%

Periodic acid, a novel oxidant of polycyclic, aromatic hydrocarbons

Fatiadi¹

1968

J. RES. NATL. BUR. STAN. SECT. A.

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Ce rtain polycyc li c , aro mat ic hydrocarbons can be ox idi zed with periodi c acid in aprotic so lvent s co nta inin g a s mall p roportion of water. A uniqu e, two· fold cha rac te r of respo nse to pe riodi c acid by these hydroca rbon s has been fo und: (1) prod uc ti on of a co uplin g reac tion throu gh a radi ca l in te rme diate [co nve rsion of pyre ne into l,l ' -b ipyrene, and fluore ne into 1,2-b is(2,2' -biph e ny lylene)ethy le neJ or (2) co nvers io n into qui no nes by a two-equiv alent ox id ation mec hani s m that does not involve a radical int erm edi a te [ace naphth e ne, anthracene, a nthrone , be nz[alanthrace ne, naphthace ne, naphthalen e, a nd ph e nanthre ne]. Little or no reac ti on was observed whe n ox idati on was attempted wi th sodium me taperiodate in s tead of pe riodi c ac id .Electron-s pin reso nan ce revea led no radi cal inte rmediate in th e ox id a ti on of malonic ac id with e ither periodic acid o r sodium periodate.Key Word s: Aproti c so lvents ; aromatic hydroca rbon s; maloni c acid ; periodic acid ; pyrene radical; quinon es; reacti on mecha ni s m; sodium metape ri oda te.

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Osmium and Ruthenium Tetroxide-Catalyzed Oxidations of Pyrene¹

Cited by 50 publications

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Synthesis, Photophysical and Electronic Properties of New Red‐to‐NIR Emitting Donor–Acceptor Pyrene Derivatives

Synthesis, Photophysical and Electronic Properties of New Red‐to‐NIR Emitting Donor–Acceptor Pyrene Derivatives

Surface Oxides of Carbon

Periodic acid, a novel oxidant of polycyclic, aromatic hydrocarbons

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Osmium and Ruthenium Tetroxide-Catalyzed Oxidations of Pyrene1

Cited by 50 publications

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Synthesis, Photophysical and Electronic Properties of New Red‐to‐NIR Emitting Donor–Acceptor Pyrene Derivatives

Synthesis, Photophysical and Electronic Properties of New Red‐to‐NIR Emitting Donor–Acceptor Pyrene Derivatives

Surface Oxides of Carbon

Periodic acid, a novel oxidant of polycyclic, aromatic hydrocarbons

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Product

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Osmium and Ruthenium Tetroxide-Catalyzed Oxidations of Pyrene¹