Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 15, Pages 9611-9626Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01290
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Funding
- EPSRC President's Scholarship
- EPSRC [1974973] Funding Source: UKRI
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Advances in the transition-metal-free cyclobutanol ring expansion to 4-tetralones under N-bromosuccinimide mediation are described. We have expanded the scope of this ring expansion methodology and investigated the effect substituents on the aromatic ring, and the cyclobutanol moiety, have on the outcome of the reaction. Limitations with certain substituents on the cyclobutanol moiety are also described. Further experimental evidence to support our mechanistic understanding is disclosed, and we now preclude the suggested involvement of a primary radical for this transformation.
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