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( Z )‐ und ( E )‐Enole von diarylsubstituierten β‐Ketocarbonsäurederivativen
Author(s) -
Buß Monika,
Mayer Axel,
Müller Klaus,
Meier Herbert
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960725
Subject(s) - chemistry , steric effects , tautomer , diazo , medicinal chemistry , stereochemistry , thermal decomposition , organic chemistry
( Z ) and ( E ) Enols of Diaryl‐Substituted β‐Ketocarboxylic Acid Derivatives Thermolysis of the 1,3‐diaryl‐2‐diazo‐1,3‐propanediones 4 in the presence of alcohols or amines yielded the compounds 7–11 which exist as chelated ( Z ) enols or as tautomeric ketones. Contrary to the steric interaction of two mesityl groups the steric interaction between two naphthyl or two anthryl groups or between naphthyl and mesityl is not sufficient to stabilize the corresponding ( E ) enols. The latter isomers were generated in irradiation processes of some ( Z ) enols. Detailed NMR studies were performed in order to characterize the enols and their molecular dynamics.