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Interrupted carbonyl-olefin metathesis via oxygen atom transfer

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Science  28 Sep 2018:
Vol. 361, Issue 6409, pp. 1363-1369
DOI: 10.1126/science.aar8238

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Two ways out of an oxetane

Oxetanes are highly reactive four-membered rings that contain three carbon atoms and an oxygen atom. Recently, they were implicated as transient intermediates in Lewis acid–catalyzed intramolecular metathesis reactions of ketones with olefins. Ludwig et al. now report that by replacing the Lewis acid with a strong Brønsted acid, they can change the course of the oxetane ring-opening. In a so-called interrupted metathesis, the oxygen atom migrates and then departs through dehydration, while the remaining carbon framework cyclizes to form tetrahydrofluorene compounds.

Science, this issue p. 1363