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Experimental and Theoretical Study of the Keto–Enol Tautomerization of 3,5‐Dioxopimelates
Author(s) -
Erfle Silke,
Reim Stefanie,
Michalik Dirk,
Jiao Haijun,
Langer Peter
Publication year - 2011
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.201100292
Subject(s) - tautomer , chemistry , enol , keto–enol tautomerism , solvent , condensation , computational chemistry , nuclear magnetic resonance spectroscopy , solvent effects , chloride , medicinal chemistry , spectroscopy , organic chemistry , catalysis , physics , quantum mechanics , thermodynamics
Substituted 3,5‐dioxopimelic acid diesters, stable 1,3,5,7‐tetracarbonyl derivatives, were prepared by condensation of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with methyl malonyl chloride. The influence of the substituents and the solvent on the keto–enol tautomerization of these compounds was investigated by NMR spectroscopy. For the parent compound, the experimental findings were compared with computational results.