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Ring-Opening Carbonyl-Olefin Metathesis of Cyclobutenes.

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The ring-opening carbonyl-olefin metathesis of cyclobutenes to furnish γ,δ-unsaturated aldehydes-formal Claisen rearrangement products-is reported. The bistrifluoroacetic acid salt of 2,3-diazabicyclo[2.2.2]octane promotes these reactions efficiently with a variety of cyclobutenes and… Click to show full abstract

The ring-opening carbonyl-olefin metathesis of cyclobutenes to furnish γ,δ-unsaturated aldehydes-formal Claisen rearrangement products-is reported. The bistrifluoroacetic acid salt of 2,3-diazabicyclo[2.2.2]octane promotes these reactions efficiently with a variety of cyclobutenes and aldehydes, including aliphatic, α,β-unsaturated, aryl, and heteroaryl aldehydes. Catalytic reactions are also demonstrated.

Keywords: olefin metathesis; carbonyl olefin; metathesis cyclobutenes; ring opening; opening carbonyl

Journal Title: ACS catalysis
Year Published: 2022

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