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Tetronic acids and derivatives. Part XI . Structure of coupling products of tetronic acids with benzenediazonium sulfate
Author(s) -
Gelin Suzanne,
Pollet Patrick
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180416
Subject(s) - chemistry , tautomer , benzene , sulfate , proton nmr , azo coupling , ascorbic acid , coupling (piping) , stereochemistry , furan , organic chemistry , medicinal chemistry , mechanical engineering , food science , engineering
13 C Nmr, 1 H nmr and ir parameters of coupling products of tetronic acids (4‐hydroxy‐5 H ‐furan‐2‐ones) with benzene diazonium sulfate are only consistent with a phenylhydrazone formulation with an almost equal ratio of the syn and anti configurations. These results contrast with those of coupling products of acyclic 3‐ketoesters, existing mainly as anti tautomers, and more sharply with the 3‐parabromophenylhydrazone of L‐dehydro ascorbic acid, which is exclusively syn .