Transition-Metal-Free Ring-Opening Reaction of 2-Halocyclobutanols through Ring Contraction,European Journal of Organic Chemistry

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Transition-Metal-Free Ring-Opening Reaction of 2-Halocyclobutanols through Ring Contraction
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2021-08-11 , DOI: 10.1002/ejoc.202100837
Petr Oeser ₁ , Tereza Edlová ₂ , Marek Čubiňák ₁ , Tomáš Tobrman ₃

Affiliation

We have developed a new procedure for the preparation of aryl alkyl ketones and α,β-unsaturated ketones by thermal opening of halocyclobutanols. The reaction conditions for the thermal isomerization of cyclobutanols depend on the relative configuration of halohydrins. Based on the experiments performed, we assume that the halocyclobutanols undergo ring contraction to form cyclopropyl ketones, which are isomerized by means of hydrogen halide.