Nucleophilic Additions to Fused Bicyclic Five-Membered Ring Oxocarbenium Ions: Evidence for Preferential Attack on the Inside Face

Journal of the American Chemical Society

Volumn 125, Issue 46, 2003, Pages 14149-14152

  Smith, Deborah M ^a   Tran, Michelle B ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILIC ADDITIONS;

POSITIVE IONS; REACTION KINETICS;

AROMATIC COMPOUNDS;

ION; OXOCARBENIUM ION; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ACETALS; BICYCLO COMPOUNDS, HETEROCYCLIC; ETHERS, CYCLIC; FURANS; MOLECULAR CONFORMATION;

EID: 0242414726     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0375176     Document Type: Article

References (38)

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34. With each Lewis acid, the counterion for the oxocarbenium ion is different, but the selectivity is independent of this counterion. In addition, because the selectivities are insensitive to the solvent, ion pairing is not evidently important.
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36. Additional details are provided as Supporting Information.
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