Base-catalyzed dehydration of 3-substituted benzene cis -1,2-dihydrodiols: Stabilization of a cyclohexadienide anion intermediate by negative aromatic hyperconjugation

Journal of the American Chemical Society

Volumn 134, Issue 34, 2012, Pages 14056-14069

  Kudavalli, Jaya Satyanarayana ^a   Rao, S Nagaraja ^a   Bean, David E ^b   Sharma, Narain D ^c   Boyd, Derek R ^c   Fowler, Patrick W ^b   Gronert, Scott ^f   Kamerlin, Shina Caroline Lynn ^d   Keeffe, James R ^e   More Oferrall, Rory A ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^d UPPSALA UNIVERSITY   (Sweden)

^e SAN FRANCISCO STATE UNIVERSITY   (United States)

^f VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLVENTS; AROMATICITIES; COMPUTATIONAL RESULTS; CONCERTED REACTIONS; EXPERIMENTAL EVIDENCE; HYDROGEN ISOTOPE EXCHANGE; HYDROXIDE IONS; HYPERCONJUGATION; LIMITING VALUES; RATE DETERMINING STEP; REACTIVE INTERMEDIATE; RING CURRENTS; ROTATIONAL RELAXATIONS; SOLVENT ISOTOPE EFFECTS; TRANSITION STATE;

AROMATIZATION; BENZENE; CATALYSIS; DEHYDRATION; HYDROGEN; ISOTOPES; NEGATIVE IONS; PHENOLS; PROTON TRANSFER; RATE CONSTANTS; STABILIZATION;

REACTION INTERMEDIATES;

1,2 DIHYDROXYCYCLOHEXADIENIDE; ANION; BASE; BENZENE CIS 1,2 DIHYDRODIOL; BENZENE DERIVATIVE; CARBON; CYCLOHEXANE DERIVATIVE; HYDROXIDE; ISOTOPE; PHENOL; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT;

ANIONS; BENZENE; CATALYSIS; CYCLOHEXENES; KINETICS; PHENOLS; WATER;

EID: 84865632608     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304366j     Document Type: Article

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