Synthesis and reactivity of octa(methoxycarbonyl)cycloheptatriene

Electron-deficient cycloheptatrienes are highly acidic compounds with versatile reactivity. A copper-catalyzed oxidative dehydrogenation is applied to synthesize octa(methoxycarbonyl)cycloheptatriene from the corresponding diene analogue. The preserved reactivity of the non-acidic triene provides key mechanistic insight, revealing a tendency to form aromatic products through pathways not contingent on Brønsted acidity.