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Mechanistic and synthetic aspects of intramolecular alkoxide–allene cyclizations
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1984
Year
EngineeringHeterocyclicBiochemistryNatural SciencesRadical (Chemistry)Synthetic AspectsVinyl EpoxideOrganic ChemistrySteric EnvironmentChemistryIntramolecular CyclizationBiomolecular Engineering
Intramolecular cyclization of the methoxyallene–alkoxide adducts (1a) proceeds along two different pathways via a methoxyallyl radical to give either a dihydrofuran, or vinyl epoxide, depending upon the steric environment of the redical anion.