An unusual thionyl chloride-promoted C-C bond formation to obtain 4,4 '-bipyrazolones

Gernot A. Eller, Gyte Vilkauskaite, Algirdas Sackus, Vytas Martynaitis, Ashenafi Damtew Mamuye, Vittorio Pace, Wolfgang Holzer (Corresponding author)

    Publications: Contribution to journalArticlePeer Reviewed

    Abstract

    The tautomerism of 1-​phenyl-​1,​2-​dihydro-​3H-​pyrazol-​3-​One was investigated. An X-​ray crystal structure anal. exhibits dimers of 1-​phenyl-​1H-​pyrazol-​3-​ol units. Comparison of NMR (NMR) spectra in liq. state (1H, 13C, 15N) with those of "fixed" derivs., as well as with the corresponding solid state NMR spectra reveal this compd. to exist predominantly as 1H-​pyrazol-​3-​ol mol. pairs in nonpolar solvents like CDCl3 or C6D6, whereas in DMSO-​d6 the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-​pyrazol-​3-​ol derivs. are presented.
    Original languageEnglish
    Pages (from-to)1287-1292
    Number of pages6
    JournalBeilstein Journal of Organic Chemistry
    Volume14
    DOIs
    Publication statusPublished - 4 Jun 2018

    Austrian Fields of Science 2012

    • 104015 Organic chemistry

    Keywords

    • dimerization
    • NMR (H-1; C-13; N-15)
    • pyrazolones
    • X-ray structure analysis
    • thionyl chloride
    • PHOTOCHEMICAL OXIDATION
    • MULTICOMPONENT REACTION
    • BIOLOGICAL-ACTIVITIES
    • HETEROCYCLIC-ANALOGS
    • PYRAZOLE
    • CHEMISTRY
    • 13C
    • Thionyl chloride
    • 15N)
    • Pyrazolones
    • NMR (1H
    • Dimerization

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