83349-67-1Relevant academic research and scientific papers
Oxidation of Polynuclear Aromatic Hydrocarbons with Ceric Ammonium Sulfate: Preparation of Quinones and Lactones
Balanikas, George,Hussain, Nalband,Amin, Shantu,Hecht, Stephen S.
, p. 1007 - 1010 (2007/10/02)
The oxidation of polynuclear aromatic hydrocarbons with ceric ammonium sulfate (CAS) in sulfuric acid was investigated.Oxidation of benzofluoranthene (1) gave a mixture of the 7,12- and 2,3-diones 3 and 4.The 2,3-dione (4) was used as the starting material for a facile synthesis of 2,3-dihydro-2,3-dihydroxybenzofluoranthene (5) and the corresponding diol epoxide 6, which are potentially important metabolites of benzofluoranthene.In a similar manner, 2,3-dihydro-2,3-dihydroxyfluoranthene (7) and its diol epoxide 8 were prepared from fluoranthene.Oxidation of benzofluoranthene (2) with CAS did not yield quinones, but instead gave benzofluorenopyran-5,13-dione (9), which was identified by its spectral properties and by reduction with LiAlH4.The lactone 9 formed via initial K-region oxidation of 2.It was not formed from 1-hydroxybenzofluoranthene (12), which gave benzofluoranthene-1,2-dione (13) upon CAS oxidation.CAS oxidation of benzopyrene (14) gave a mixture of the 1,6- and 3,6-quinones 17 and 18.Treatment of benzanthracene (15) with CAS yielded 7-oxo-12-hydroxy-7,12-dihydrobenzanthracene (19) and the 7,12-quinone 20.Oxidation of chrysene (16) with CAS gave 6H-benzonaphthopyran-6-one (21) and the 5,6-quinone 22.The results of this study demonstrate that CAS oxidation is useful for the synthesis of certain PAH quinones or lactones, from polynuclear aromatic hydrocarbons, depending on the ring system.
Fluoranthene: Synthesis and Mutagenicity of Four Diol Epoxides
Rastetter, William H.,Nachbar, Robert B.,Russo-Rodriguez, Sandra,Wattley, Ruth V.,Thilly, William G.,et al.
, p. 4873 - 4878 (2007/10/02)
The syntheses of diol epoxides 4a,b and 5a,b of the mutagenic hydrocarbon fluoranthene (1) are described.Standard methodology is applied to the synthesis of targets 4a,b but fails for the synthesis of 5a,b.The latter two diol epoxides can be assembled by a route utilizing stereoselective, directed epoxidations.Simple molecular orbital calculations have been used to predict the reactivity of the diol epoxides in their opening to triol carbocations.Diol epoxides 4a,b are predicted to be substantially more reactive than isomers 5a,b.The more reactive pair, 4a,b, mayyield carbocations capable of alkylating cellular genetic material.This prediction is borne out in terms of the relative mutagenicity of the diol epoxides in a bacterial screen.
