Investigations into the role of ion pairing in reactions of heteroatom-substituted cyclic oxocarbenium ions.
[reaction: see text] The O-to-C rearrangement of vinyl acetals is used to demonstrate that tight ion pairing is not involved in the stereoselective nucleophilic addition reactions of alkoxy-substituted cyclic oxocarbenium ions.
Shenoy
Siddhartha R
SR
Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006838:Hydrocarbons / Q000737:chemistry; D007202:Indicators and Reagents; D007477:Ions / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000080:Acetals; D006838:Hydrocarbons; D007202:Indicators and Reagents; D007477:Ions; C030011:carbene; D008697:Methane