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Die Enonamin‐Enolimin‐Tautomerie
Author(s) -
Grob C. A.,
Wilkens H. J.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500302
Subject(s) - chemistry , tautomer , intramolecular force , aromaticity , cyclohexanone , hydrogen bond , ultraviolet , infrared , computational chemistry , stereochemistry , organic chemistry , molecule , catalysis , physics , quantum mechanics , optics
A study of the ultraviolet, infrared, and nuclear magnetic resonance spectra of Δ 8,9 ‐octahydro‐7‐quinolone ( 7a ) and of the corresponding N‐ and O‐ethyl derivatives 8 and 9 , respectively, confirms that in cases of potential enonamine‐enolimine tautomerism the enonamine form predominates. This also applies to vinylogous amides capable of intramolecular hydrogen bonding, such as 2‐benzylaminomethylene‐ and 2‐phenylaminomethylene‐cyclohexanone, 10 and 11 , respectively. Exeptions are only observed in cases where the enolimine form is stabilized by special factors, such as aromaticity.