Abstract
Schönberg and Mustafa [1,2] found that aromatic substituted ethylenes (e.g. styrene, stilbene, triphenylethylene) undergo an addition reaction with phenanthrenequinone (1) in benzene solution under the influence of light: The reaction with stilbene (2) leads to formation of 2,3-dihydro-2,3-di-phenylphenanthro[9,10-b][l,4]dioxin (3), the constitution of which was derived from its lack of color and its facile (270°) decomposition to phenanthrenequinone and stilbene as well as from the formation of phenanthrenequinone by the action of concentrated sulfuric acid on 3. Compound 3 was later obtained in a dark process by Butenandt et al. [3].
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References
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Schönberg, A. (1968). Photochemical cycloaddition of 1,2-quinones, 1,2-diketones and 1,2,3-triketones to multiple bonds. In: Preparative Organic Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87918-0_12
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DOI: https://doi.org/10.1007/978-3-642-87918-0_12
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