Tetrahedron Letters p. 2735 - 2738 (1984)
Update date:2022-08-04
Topics:
Gollnick, Klaus
Schnatterer, Albert
Electron-rich 1,1-diarylethylenes (1a-e) afford 3,3,6,6-tetraaryl-1,2-dioxanes (3a-e) in high yields (>90percent) when subjected to electrontransfer photooxygenation in the presence of DCA.Whereas 1,1-diphenylethylene (1f) and 1,1-di(p-chlorophenyl)ethylene (1h) yield the 1,2-dioxanes 3f and 3h at 30percent and less than 10percent, respectively, there is negligible (if any) 1,2-dioxane formation with 1,1-di(m-anisyl)ethylene (1i). 1,2-Dioxane formation proceeds in a chain reaction (Scheme 1).N-Vinylcarbazol (1g), however, yields the 1,2-dioxane 3g via the cyclobutane derivative 7 (Scheme 2).
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