title: Oxidative cyclization reactions: controlling the course of a radical cation-derived reaction with the use of a second nucleophile.
abstract: Construction of new ring systems: Oxidative cyclizations (see picture; RVC=reticulated vitreous carbon) have been conducted that use two separate intramolecular nucleophiles to trap an enol ether-derived radical cation intermediate. The reactions provide a means for rapidly trapping the radical cation intermediate in a manner that avoids competitive decomposition reactions.
authors.affiliation: Department of Chemistry, Washington University in St. Louis, St. Louis, MO 63130 (USA).
authors.forename: Alison
authors.initials: A
authors.lastname: Redden
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Perkins
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Moeller
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002412:Cations / Q000737:chemistry; D003500:Cyclization; D004563:Electrochemistry; D005609:Free Radicals / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D002412:Cations; D005609:Free Radicals; D006844:Hydrocarbons, Cyclic
keywords: anodic cyclizations; electrochemistry; radical ions; reactive intermediates