Ozonation of Carbon-Hydrogen Bonds. Anthrone

Batterbee, J. E.; Bailey, Philip S.

doi:10.1021/jo01287a601

Cited by 19 publications

(14 citation statements)

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“…Maloni c acid (14), which has an ac ti ve methylene group , was a lso ox idized. In addition, the following co nd e nsed-rin g, polycyclic, aromatic hydrocarbons we re tested: biph e nyl , c hrysene, co ro nene, Au oranthe ne, perylene, picene, p-terphenyl, and triph e nyle ne .…”

Section: Compounds Oxidizedmentioning

confidence: 99%

“…The attack by a monoanion of periodic acid on a methyl e ne group of 8 is a type of in se rtion of a li gand oxyge n atom into a C-H bond ; thi s may possibly be the way in which the active oxyge n of pe riodic acid is tra nsfe rred; an alternativ e way, postulating th e in se rtion of an unbound oxyge n atom, was s ugges ted by Bunton [74]. The in sertion mechanism in the ozone ox idation of flu ore ne o r a nthrone has recently been proposed [14].…”

Section: General Reactivity Of Polycyclic Aromaticmentioning

confidence: 99%

“…Oxidation of malonic acid (14) with periodic acid or sodium period ate has been thoroughly studied [35,75] id e ntifi ed [35 , 75]. Assuming that products 14b and 14c arise from 14 , as reported [35,75], this oxidative cleavage reaction has been checked for possible participation of free radicals.…”

Section: Oxidation Of Malonic Acid (14)mentioning

confidence: 99%

“…By means of e.s. r. meas urements, hydroxylation of malonic acid (14) with pe ri odi c acid and sodium periodate was examined in wate r ; monitoring of the reaction path (at 0 to 60°C) did not reveal free radicals, in agreement with an earli e r ob- It is also believed that the reported [35,75] hydroxylation of an active methylene group in malonic acid (14) and its derivatives by periodic acid ·or sodium periodate in aqueous solution also proceeds by a ligand push-pull mechanism, similar to that described for anthrone (8) (see sec. 3.8), although direct transfer of an oxygen atom by periodate to the active methylene group of malonic acid (electrophilic oxidation) has also been proposed [74].…”

Section: Oxidation Of Malonic Acid (14)mentioning

confidence: 99%

“…Malon ic Acid (14) An aliquot (0.4 ml) of maloni c acid (0.3 M, in water) was mixed in the cell with two drops of aqueous periodic acid (0.5 M) at room temperature; th e e.s.r. spectrum did not reveal any radicals; warming (hot-water bath) or cooling (ice-bath) of the cell and scanning of (he spectrum did not reveal any radicals.…”

Section: Oxidation Of Acenaphthene (15) Tomentioning

confidence: 99%

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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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Section: Compounds Oxidizedmentioning

confidence: 99%

Section: General Reactivity Of Polycyclic Aromaticmentioning

confidence: 99%

Section: Oxidation Of Malonic Acid (14)mentioning

confidence: 99%

Section: Oxidation Of Malonic Acid (14)mentioning

confidence: 99%

Section: Oxidation Of Acenaphthene (15) Tomentioning

confidence: 99%

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Periodic acid, a novel oxidant of polycyclic, aromatic hydrocarbons

Fatiadi¹

1968

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

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Novel aspects of carbonyl oxide chemistry

Ishiguro

Nojima

Sawaki

1997

J. Phys. Org. Chem.

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The structural and chemical properties of 1,3-dipolar peroxidic species (X-O-O) such as ozone (X = O) and carbonyl oxides (X = R 2 C) depend significantly on the nature of X. Although cyclic O 3 is thermodynamically unstable, dioxiranes, cyclic isomers of carbonyl oxides, are isolable and have been fully characterized. In contrast to the well known electrophilic nature of ozone, carbonyl oxides usually act as a nucleophilic oxygen transfer agent, but their reactivity could be altered by substituents. It is expected that the chemistry of R 2 C-O 2 species will provide a good starting point for a better understanding of dioxygen complexes (X-O 2 ) with various Xs. Interesting aspects of carbonyl oxide chemistry are discussed, including methods of generation, cyclization to dioxiranes and the nature of their oxygen transfer activities.

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Peroxide intermediates of oxidation processes: Organic trioxides

Khursan

2014

Patai's Chemistry of Functional Groups

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The review discusses the results of studies on the chemistry of organic trioxides ROOOR (R = H or an organic radical) carried out in the past years. The spectral identification, structure, thermal stability and chemical properties of HOOOH, HOOO ⋅ , hydrotrioxides, open‐chain and cyclic trioxides (including fullerene ozonides) are described. The significance of trioxides for biochemistry, environmental chemistry, and organic synthesis is much higher than it was believed previously. The chemical reactions that these compounds undergo resemble those of peroxides. However, the temperature range in which trioxide reactions occur is shifted considerably towards low temperatures. Homolytic decomposition at one of the OO bonds is the most typical reaction of trioxides. Trioxides are liable to induced and catalytic decomposition. Hydrotrioxides demonstrate high oxidative activity. Decomposition of some trioxides is accompanied by efficient generation of singlet oxygen.

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Ozonation of Carbon-Hydrogen Bonds. Anthrone

Cited by 19 publications

References 0 publications

Periodic acid, a novel oxidant of polycyclic, aromatic hydrocarbons

Periodic acid, a novel oxidant of polycyclic, aromatic hydrocarbons

Novel aspects of carbonyl oxide chemistry

Peroxide intermediates of oxidation processes: Organic trioxides

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