Reactivity of nitrovinylquinones with cyclic and acyclic enol ethers

Wayland E Noland, Brant L. Kedrowski

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19 Scopus citations


The nitrovinyl-substituted quinones 2-(2-nitrovinyl)-1,4-benzoquinone and 2-(2-nitrovinyl)-1,4- naphthoquinone react with a variety of cyclic and acyclic enol ethers via two competing pathways. In one pathway, the nitrovinylquinone acts as an inverse electron-demand [4 + 2] diene. This gives quinoid carbocycles, which readily tautomerize to their hydroquinone form. The other pathway involves conjugate (Michael) addition of the enol ether to the nitrovinylquinone, followed by ring closure. This gave dihydrobenzofurans, which can eliminate an alcohol to give benzofurans. Hindered enol ethers tended to favor the conjugate addition pathway, while less hindered enol ethers favored cycloaddition.

Original languageEnglish (US)
Pages (from-to)8366-8373
Number of pages8
JournalJournal of Organic Chemistry
Issue number24
StatePublished - Nov 29 2002


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