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The Tautomeric Persistence of Electronically and Sterically Biased 2‐Quinolinones
Author(s) -
Volle JeanNoël,
Mävers Ursula,
Schlosser Manfred
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800123
Subject(s) - tautomer , chemistry , steric effects , stereochemistry , lactam , computational chemistry
One dozen of tailormade model 3‐fluoro‐2(1 H )‐quinolinones were synthesized in order to be investigated by UV‐, IR‐ and NMR spectroscopic techniques. All of these compounds were found to exist predominantly, if not exclusively, in the lactam (carboxamide, 1,2‐dihydro‐2‐oxoquinoline) form. No tautomeric lactim (iminol, azaphenol) structure was detected. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)