Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Product Studies by HPLC on the Hydrolysis of the anti- and syn-Tetrahydrodiol Epoxides and the 1,2-Tetrahydro Epoxide of Naphthalene

  • Published : 1997.08.20
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Abstract

The arene epoxides from naphthalene, 1β,2α-dihydroxy-3α,4α-epoxy- (1) and 1β,2α-dihydroxy-3β,4β-epoxy-1,2,3,4-tetrahydronaphthalene (2) (anti- and syn-diol epoxide), 1,2-epoxy-1,2,3,4-tetrahydronaphthalene (3), and 1,2-epoxy-l,2-dihydronaphthalene (4), are model compounds of the ultimate carcinogenic metabolites of polycyclic aromatic hydrocarbons, ubiquitous environmental pollutants which may be causal in several human cancers. The product distribution in the hydrolysis of 1-4 have been studied by HPLC analysis of reaction mixtures. The yields of the trans product from the hydronium-ion-catalyzed and pH-independent hydrolysis in 9 : 1 (v/v) 20 mM buffer-dioxane at 25 ℃, respectively, were; 1: 98, 100; 2: 74, 87, 3: 95, 97, 4:100, 100. The results were rationalized by conformational equilibria of the epoxides and the carbocationic and zwitterionic intermediates from the epoxides.

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