Using stereoelectronic effects to explain selective reactions of 4-substituted five-membered ring oxocarbenium ions.
[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.
Smith
Deborah M
DM
Department of Chemistry, University of California-Irvine, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
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
D000080:Acetals; D006838:Hydrocarbons; D007477:Ions; C030011:carbene; D008697:Methane