Aromatic Cope rearrangements

Breanna M. Tomiczek, Alexander J. Grenning

Research output: Contribution to journalReview articlepeer-review

11 Scopus citations

Abstract

Reviewed herein is the aromatic Cope rearrangement, a Cope rearrangement where one (or both) of the alkenes of the 1,5-diene are part of a greater aromatic system. While the Cope rearrangement of 1,5-dienes has seen wide utility, variation, and application in chemical synthesis, the aromatic Cope rearrangement, comparatively, has not. This review summarizes the ∼40 papers dating back to 1956 on this topic and is divided into the following sections: (1) introduction, including kinetic and thermodynamic challenges of the aromatic Cope rearrangement, and (2) key substrate features, of which there are four general types: (i) α-allyl-α-aryl malonates (and related substrates), (ii) 1-aryl-2-vinylcyclopropanes, and (iii) anion-accelerated aromatic oxy-Cope substrates, and (iv) the concept ofsynchronized aromaticity. Ultimately, we hope this review will draw attention to a potentially valuable transformation for arene functionalization that warrants further studies and development.

Original languageEnglish (US)
Pages (from-to)2385-2398
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number11
DOIs
StatePublished - Mar 21 2021
Externally publishedYes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2021.

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