Not antiaromaticity gain, but increased asynchronicity enhances the Diels–Alder reactivity of tropone†
Abstract
Tropone is an unreactive diene in normal electron demand Diels–Alder reactions, but it can be activated via carbonyl umpolung by using hydrazone ion analogs. Recently, the higher reactivity of hydrazone ion analogs was ascribed to a raised HOMO energy induced by antiaromaticity (L. J. Karas, A. T. Campbell, I. V. Alabugin and J. I. Wu, Org. Lett., 2020, 22, 7083). We show that this is incorrect, and that the activation barrier is lowered by increased asynchronicity.
- This article is part of the themed collection: Chemical Communications HOT Articles 2023
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