Ring-Opening Carbonyl-Olefin Metathesis of Cyclobutenes
Maxwell G. Holl, Tristan H. Lambert
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.
Topics & Concepts
Olefin metathesisChemistryOctaneMetathesisCatalysisRing (chemistry)Salt (chemistry)Olefin fiberArylSalt metathesis reactionOrganic chemistryMedicinal chemistryAlkylPolymerizationPolymerSynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisModel-Driven Software Engineering Techniques