Intramolecular cycloaddition reactions of α-bromostyrene-functionalized amides of monomethyl fumarate were investigated. The reaction of the amides with Et<sub>3</sub>N in toluene at 110 °C gave 1,4-dihydronaphthalenes. The 1,4-dihydronaphthalenes may be produced via intramolecular Diels-Alder reaction, proton transfer, dehydrobromination by base, along with C=C bond isomerization by proton transfer. The reaction of amide derivatives with halogen on benzene ring and alkali metal carbonates in toluene at 110 °C gave naphthalene derivatives directly. Dehydrogenation of various 1,4-dihydronaphthalenes with cesium or rubidium carbonate in toluene at 110 °C gave naphthalene derivatives. The retardation by TEMPO, acceleration by air for some substrates, and DFT calculations suggest radical mechanism caused by intervention of molecular oxygen.

Intramolecular Diels-Alder reactions of α-Bromostyrene-functionalized unsaturated carboxamides

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