Activation of electrophilicity of stable Y-delocalized carbamate cations in intramolecular aromatic substitution reaction: Evidence for formation of diprotonated carbamates leading to generation of isocyanates

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9313-9328

  Kurouchi, Hiroaki ^a   Kawamoto, Kyoko ^a   Sugimoto, Hiromichi ^a   Nakamura, Satoshi ^a   Otani, Yuko ^a   Ohwada, Tomohiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID MEDIA; AROMATIC RINGS; AROMATIC SUBSTITUTION REACTIONS; CYCLIZATION REACTIONS; DICATIONS; ELECTROPHILICITY; ENTROPY OF ACTIVATION; FIRST ORDER REACTIONS; HETEROATOMS; HIGH YIELD; LINEAR RELATIONSHIPS; METHYL CARBAMATE; MONOCATIONS; PROTONATED; RATE DETERMINING STEP; REACTION MEDIUM; SHARP CONTRAST; STRONG ACIDS; WEAK BASIS;

AROMATIC COMPOUNDS; METHANOL; POSITIVE IONS; PROTONATION; SUBSTITUTION REACTIONS; UREA;

CYCLIZATION;

2 2 CHLOROPHENYLETHYLCARBAMIC ACID METHYL ESTER; 2 2 FLUOROPHENETHYLCARBAMIC ACID METHYL ESTER; 2 3 CHLOROPHENETHYLCARBAMIC ACID METHYL ESTER; 2 3 FLUOROPHENETHYLCARBAMIC ACID METHYL ESTER; 2 3 NITROPHENYLETHYLCARBAMIC ACID METHYL ESTER; 2 3 TOLYLETHYLCARBAMIC ACID METHYL ESTER; 2 4 CHLOROPHENETHYLCARBAMIC ACID METHYL ESTER; 2 4 FLUOROPHENETHYLCARBAMIC ACID METHYL ESTER; 2 4 METHOXYPHENYLETHYLCARBAMIC ACID METHYL ESTER; 2 4 NITROPHENYLETHYLCARBAMIC ACID METHYL ESTER; 2 4 TOLYLETHYLCARBAMIC ACID METHYL ESTER; 2,4 DICHLOROPHENETHYLCARBAMIC ACID METHYL ESTER; 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 5 CHLORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 5 FLUORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 6 CHLORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 6 FLUORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 6 METHYL 3,4 DIHYDRO 2H ISOQUINOLIN 1 ON; 7 CHLORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 7 FLUORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 7 HYDROXY 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 7 METHYL 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 8 CHLORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 8 FLUORO 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; 8 METHYL 3,4 DIHYDRO 2H ISOQUINOLIN 1 ONE; [2 (2 FLUORO 5 METHYL PHENYL)ETHYL]CARBAMIC ACID METHYL ESTER; CARBAMIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PHENETYLCARBAMIC ACID METHYL ESTER; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROPHILICITY; ENTROPY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SUBSTITUTION REACTION;

CARBAMATES; CATIONS; ISOCYANATES; MOLECULAR STRUCTURE; PROTONS;

EID: 84867730257     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3020566     Document Type: Article

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