Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert

Abstract

Reactions of 2-arylcyclopropane dicarboxylates with naphthoquinones are reported. The key feature was the use of catalytic amounts of SnCl₂ , which acts as both an electron donor and a Lewis acid. By an in situ umpolung of naphthoquinone the formerly electrophilic species is converted into a nucleophile that is able to trigger the ring-opening of the three-membered ring with formation of a new C-C bond. Treatment of these products with base under oxidative conditions resulted-through loss of methyl formate-in cyclopentannulated products with fully conjugated π systems exhibiting intensive absorptions in the visible range.

Keywords: annulation; cyclopropanes; donor-acceptor systems; naphthoquinone; tin.