- Reactions of the K-Region Epoxides of Polycyclic Aromatic Hydrocarbons with Phosphodiesters. A Potential Detoxification Reaction
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Phenanthrene 9,10-oxide reacts with diethyl hydrogen phosphate to give 9-phenanthrol.The reaction was first order in both epoxide and phosphate concentrations, with a pseudo-first-order rate constant kφ = 6.2e-1 mol-1Ls-1.Similarly, chrysene 5,6-oxide on reaction with phosphate opened regiospecifically to give 6-chrysenol.Several anilinium phosphate salts were prepared and reacted with phenanthrene 9,10-oxide.The extent of reaction was markedly influenced by the pKa of the anilinium salt.The biological implications of this study in understanding the relative noncarcinogenicity of K-region arene oxides are discussed.
- Raddo, P. Di,Chan, T.H.
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- The reaction of dimethyldioxirane with chrysene: Formation of a trioxide
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Oxidation of chrysene with dimethyldioxirane gives a number of products including the interesting trioxide, chrysene-5,6:4b, 10b:11,12-trioxide, 3. The x-ray crystallographic structure of 3 indicates that it is a non-planar system.
- Murray, Robert W.,Singh, Megh,Rath, Nigam
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p. 8671 - 8674
(2007/10/03)
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- Arene Imine Derivatives of Chrysene and of Benzochrysene: 1a,11c-Dihydrochrysenoazirine and 1a,13c-Dihydrobenzochrysenoazirine
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The syntheses of the K-imines (which are also benzo-bay-region derivatives) of chrysene (1) and benzochrysene (2) are described.The preparation of 1a,11c-dihydrochrysenoazirine (5) was accomplished by treatment of 1a,11c-dihydrochrysenooxirene (4) with sodium azide, and the mixture of trans-azido-alcohols 6 and 7, so formed, was either cyclized with triethyl phosphite, or converted into E-6-azido-5-chloro-5,6-dihydrochrysene (8) followed by lithium aluminium hydride reduction.The synthesis of 1a,13c-dihydrobenzochrysenoazirine (12) included the transformation of the corresponding oxide 11 into a mixture of E-9-azido-9,10-dihydrobenzochrysen-10-ol (13) and E-10-azido-9,10-dihydrobenzochrysen-9-ol (14), and reaction with tri-n-butylphosphine to give a mixture of Staudinger adducts 15 and 16 that underwent thermal decomposition into 12 upon heating in boiling dichloromethane.
- Abu-Shqara, Elias,Elg'amal, Shafea,Blum, Jochanan
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p. 1681 - 1684
(2007/10/02)
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- FACILE SYNTHESIS OF K-REGION ARENE OXIDES
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Polycyclic aromatic hydrocarbons reacts at the K-region with N-bromoacetamide in acetic acid to provide trans-bromohydrin acetates which are readly cyclized to arene oxides.The simplicity of the approach makes radioactive and optically active K-region arene oxides easily available.
- Bladeren, P. J. van,Jerina, D. M.
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p. 4903 - 4906
(2007/10/02)
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