Abstract:
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.
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