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Keto‐Enol Tautomeric Equilibrium in 4‐Oxo‐1,1,3‐Cyclohexanetricarboxylic Acid Trialkyl Esters and 4‐Oxo‐1, 1, 3‐Cyclopentanetricarboxylic Acid Trialkyl Esters
Author(s) -
Yang ChiaHsi,
Yu Hwa,
Wu JiinSheng
Publication year - 1990
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199000055
Subject(s) - chemistry , tautomer , enol , intramolecular force , ring (chemistry) , keto–enol tautomerism , hydrogen bond , medicinal chemistry , stereochemistry , organic chemistry , molecule , catalysis
4‐Oxo‐1,1,3‐cyclohexanetricarboxylic acid trialkyl esters in deuterochloroform and dimethylsulfoxide‐d 6 (DMSO) exist exclusivly in the enol form. The keto form is the major component in the analogous compounds of five‐membered ring. The 1, 3 interaction between carboalkoxy groups in the six‐membered ring should be the reason why the carboalkoxy group at 3‐position is in equatorial configuration and engages in the intramolecular hydrogen bond, so that the enol form is dominating.