Evidence for the formation of oxaziridines during the irradiation of oximes

Oine, Toyonari; Mukai, Toshio

doi:10.1016/s0040-4039(01)87497-9

Cited by 36 publications

(8 citation statements)

References 12 publications

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“…If chlorine-free solutions of oxaziridine 7 containing less unreacted cyclohexanone are required, the compound can be obtained from the reaction of hydroxylamine- O -sulfonic acid with cyclohexanone and sodium hydroxide. 28 In addition, N -H oxaziridines have also been obtained via photolysis of hydroxylamines, 29 oxidation of ketimines by peracid, 30 and ozonolysis in the presence of ammonia. 31 …”

Section: Synthesis and Physical Properties Of Oxaziridinesmentioning

confidence: 99%

Advances in the Chemistry of Oxaziridines

2014

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Section: Synthesis and Physical Properties Of Oxaziridinesmentioning

confidence: 99%

Advances in the Chemistry of Oxaziridines

2014

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“…dCj2 Ct C signal6 dans la photolyse des nitrones (13,14), des dine peut &tre expliquee par une polarisation de la liaison aldoximes et cetoximes (13,15 …”

Section: Effet De Longueur D'ondeunclassified

Comportement photochimique du 4-nitrosophénol en solution aqueuse

Pilichowski¹,

Boule²,

Billard³

1995

Can. J. Chem.

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RksumC : En milieu acide (pH = 1) le 4-nitrosophCno1 irradiC entre 296 et 366 nm se transforme majoritairement (75580%) en benzoquinone. Le rendement quantique de cette reaction depend de la longueur d'onde : il est environ 6 fois plus Clevt k 365 nm qu'k A 5 313 nm. Ce phtnomkne est attribut k un Cquilibre tautomtrique entre les formes nitroso et quinone monooxime, la premikre Ctant photochimiquement beaucoup plus rtactive que la seconde. Dans l'eau distillee non tamponnCe (pH = 5-6), il apparait une espkce intermediaire qui prCsente en CLHP un temps de retention voisin de celui de la benzoquinone et dont le maximum d'absorption est situk ? I 235 nm. La transformation de cet intermkdiaire est acctltrCe en milieu acide.Mots elks : photochimie, 4-nitrosophCno1, effet de longueur d'onde. Abstract:In acidic medium (pH = 1) 4-nitrosophenol irradiated in the range 296-366 nm is mainly transformed into benzoquinone (75-80%). The quantum yield of this reaction is wavelength dependent: it is about 6 times higher at 365 nm than at A 5 3 13 nm. This phenomenon is attributed to an equilibrium between two tautomeric forms, nitroso and quinone monooxime, the former being much more photoreactive than the latter. In unbuffered aqueous solution (pH = 5 4 ) the formation of an intermediate is observed. Its HPLC retention time is just a little shorter than that of benzoquinone and the maximum of its absorption band is located at 235 nm. The rate of transformation of this intermediate increases with decreasing pH.

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“…At first, we investigated the photoreaction of 1,1-dimethy1-2-naphtha1enone oxime (1) (ref. 2) expecting to observe a photo-a-cleavage reaction mechan~t~ ca11y sTmi1ar to the Type I c1eavage reaction of carbony1 compounds. Contrary to our expectation, we noted good evidence for the formation of an oxaziridine intermediate which bad been suggested (ref.…”

Section: Introduction and Historical Background Of Our Studiesmentioning

confidence: 99%

Photochemical and thermal reactions of some heterocycles containing C=N-O or N=C-O group

Mukai¹,

Kumagai²,

Seshimoto³

1977

Pure and Applied Chemistry

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-In connection with photochemistry of the nonconstra1ned Ph-C=N-0 system, those of severa1 2-isoxazo1ine derivatives containing cyc1obutene, cyc1obutane, cyclopropane and cyc1ohexane rings, have been investigated as the mode1s of the rigid and constrained Ph-C=N-0 system. In most cases, such 2-isoxazo1ines, upon irradiation, underwent the nitrogenoxygen bond fission as the primary process, and produced a variety of products depending on the structures of the starting materia1s. For instance, the irradiation of 4~ary1-2-oxa-3-azabicyc1o[3.2.0]hepta-3,6-dienes afforded 2-ary1-1,3-oxazepines, sometimes accompanied by pyrro1e a1dehydes, whereas 2-isoxazo1ines fused with sma11 ring yie1ded ß-aminoa1dehydes, oxazo1ines, azirine a1dehydes, and sma11 fragments such as benzonitri1e. The photochemica1 reaction mechanismsof severa1 2-isoxazo1ines have been studied using 1ow-temperature technique. In addition, the pyro1ytic reactions of 4-pheny1-2-oxa-3-azabicyc1o[3.2.0]heptadiene and 1,3-oxazepines as we11 as their va1ence isomers have been examined to compare with their photochemica1 behavior. It was found that in pyro1ysis of bicyc1o[3.2.0]heptadiene derivatives containing the C=N-0 or N=C-0 gnoup, the cyc1obutene ring fission occurs prior to the nitrogen-oxygen or carbon-oxygen bond c1eavage. Reaction mechanisms for the deep-seated rearrangements of the 1,3-oxazepines and of 2-oxa-3-azabicyclo[3.2.0]hepta-3,6-dienes to pyrro1e a1dehydes were discussed. The resu1ts indicate the major differences in the chemica1 behaviors of the photo1yti-ca11y and therma11y excited states for those heterocyc1es.

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Evidence for the formation of oxaziridines during the irradiation of oximes

Cited by 36 publications

References 12 publications

Advances in the Chemistry of Oxaziridines

Advances in the Chemistry of Oxaziridines

Comportement photochimique du 4-nitrosophénol en solution aqueuse

Photochemical and thermal reactions of some heterocycles containing C=N-O or N=C-O group

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