Reactions of Anodically Generated Methoxystilbene Cation Radicals: The Influence of Ortho-Substituted Vinyl and Formyl Groups

2019 
The present investigation represents a continuation of studies on the effect of ortho′-substitution on the reactivity of anodically generated methoxystilbene cation radicals. Whereas previous studies have focused on the effect of ortho′-substituted nucleophilic groups such as OH, NH2, CH2OH, CH2NH2, and COOH, the present study extends the investigation to ortho′-substituted vinyl and formyl groups. The results show that when the ortho′-substituent is a vinyl group, the products include a bisdihydronaphthalene derivative and a doubly bridged, dibenzofused cyclononane from direct trapping of a bis carbocation intermediate. In the presence of an additional 3-methoxy substituent, the products are the tetracyclic chrysene derivatives. When the ortho′-substituent is a nonnucleophilic formyl group, the products include fused indanylnaphthalenes and indanylbenzopyran aldehydes. When an additional 3-methoxy group is present, an unusual fused benzofluorene-dibenzoannulene product is obtained. Mechanistic rationaliz...
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