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.
| Original language | English |
|---|---|
| Pages (from-to) | 3703-3706 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 59 |
| Issue number | 25 |
| Early online date | 27 Feb 2023 |
| DOIs | |
| Publication status | Published - 28 Mar 2023 |
Bibliographical note
Publisher Copyright:© 2023 The Royal Society of Chemistry
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