Fluoranthene: synthesis and mutagenicity of four diol epoxides

The syntheses of diol epoxides and of the mutagenic hydrocarbon fluoranthene are described. Simple molecular orbital calculations have been used to predict the reactivity of the diol epoxides in their opening to triol carbocations. Diol epoxides are predicted to be substantially more reactive than i...

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Bibliographic Details
Published in:Journal of organic chemistry 1982-12, Vol.47 (25), p.4873-4878
Main Authors: Rastetter, William H, Nachbar, Robert B, Russo-Rodriguez, Sandra, Wattley, Ruth V, Thilly, William G, Andon, Barbara M, Jorgensen, William L, Ibrahim, Mustafa
Format: Article
Language:English
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Summary:The syntheses of diol epoxides and of the mutagenic hydrocarbon fluoranthene are described. Simple molecular orbital calculations have been used to predict the reactivity of the diol epoxides in their opening to triol carbocations. Diol epoxides are predicted to be substantially more reactive than isomers. The more reactive pair, may yield 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00146a011