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A Spectroscopic and Mechanistic Study of the Enolization and Diol Formation of Hexafluoroacetylacetone in the Presence of Water and Alcohol
Author(s) -
Aygen Sitke,
van Eldik Rudi
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891220218
Subject(s) - chemistry , keto–enol tautomerism , adduct , diol , alcohol , methanol , isopropyl alcohol , stereochemistry , spectroscopy , nuclear magnetic resonance spectroscopy , medicinal chemistry , tautomer , computational chemistry , photochemistry , organic chemistry , physics , quantum mechanics
The reactions of hexafluoroacetylacetone (hfac) ( 6 ) with water, methanol, ethanol, and isopropyl alcohol were studied in detail using 1 H‐, 13 C‐, 17 O‐, 19 F‐NMR, und UV‐VIS spectroscopy. The reported spectra enable the identification of intermediate and product species, and allow a mechanistic analysis of the enolization and diol formation. The suggested mechanisms are discussed with reference to earlier data reported in the literature. An important feature of this study is the direct evidence presented for the formation of the adduct species hfac(OH) 4 ( 10 ), hfac(OMe) 2 ( 13a ), and hfac(OEt) 2 ( 13b ).