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Physical and chemical properties of hydroxyflavones. V. Deuteroxyflavones from acetoxyflavones by imidazole‐catalyzed deacetylation
Author(s) -
Looker J. H.,
Kagal S. A.,
Edman J. R.
Publication year - 1966
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.5570030113
Subject(s) - chemistry , deuterium , imidazole , hydrolysis , oxide , catalysis , infrared spectroscopy , infrared , inorganic chemistry , organic chemistry , physics , quantum mechanics , optics
A recently described procedure for imidazole‐catalyzed deacetylation of acetoxyflavones has been modified by effecting hydrolysis in a mixture of deuterium oxide and deuterioethanol (C 2 H 5 OD), or in deuterium oxide and deuteriomethanol (CH 3 OD). Application of the new procedure to monoacetoxyflavones has resulted in the monodeuteroxyflavone. 5‐Deuteroxyflavone has been obtained also by hydrolysis of a rubidium salt in deuterium oxide. Imidazole‐catalyzed hydrolysis of four diacetoxyflavones in a mixture of deuteriomethanol and deuterium oxide is described. Infrared spectral data are presented for the deuteration products, with emphasis on OD stretching and vibrational modes. Comparison of spectra of appropriate monohydroxyflavones and monodeuteroxyflavones permits assignment of δ (OH) bands in four hydroxyflavone spectra.