title: Using stereoelectronic effects to explain selective reactions of 4-substituted five-membered ring oxocarbenium ions.
abstract: [reaction: see text] The utility of the inside attack model to predict and analyze the stereoselectivities of nucleophilic additions to complex five-membered ring oxocarbenium ions is demonstrated in a systematic study of C-4-substituted acetals.
authors.affiliation: Department of Chemistry, University of California-Irvine, Irvine, California 92697-2025, USA.
authors.forename: Deborah M
authors.initials: DM
authors.lastname: Smith
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D000080:Acetals / Q000138:chemical synthesis*; D006838:Hydrocarbons; D007477:Ions / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D006838:Hydrocarbons; D007477:Ions; C030011:carbene; D008697:Methane