Mechanism of the acid-promoted intramolecular Schmidt reaction: Theoretical assessment of the importance of lone pair-cation, Cationπ, and steric effects in controlling regioselectivity

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 640-647

  Gutierrez, Osvaldo ^a   Aubé, Jeffrey ^b   Tantillo, Dean J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUPS; ANTIPERIPLANAR; AZIDOHYDRIN; LEAVING GROUPS; REGIOCONTROL; STERIC EFFECT;

CHEMICAL REACTIONS; POSITIVE IONS; REACTION INTERMEDIATES;

DENSITY FUNCTIONAL THEORY;

2 AZIDOPROPYLCYCLOHEXANONE DERIVATIVE; CATION; CYCLOHEXANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DENSITY FUNCTIONAL THEORY; REGIOSELECTIVITY; SCHMIDT REACTION; STEREOSPECIFICITY;

ACIDS; CATALYSIS; CATIONS; CYCLOHEXANONES; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 84855560621     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202338m     Document Type: Article

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