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Synthesis of polyynes by dehydrohalogenation of chlorinated paraffins
Authors:F Cataldo
Abstract:A mixture of chlorinated iso- and n-paraffins having from 22 up to 30 carbon atoms and 70% chlorine content was dehydrohalogenated with alcoholic solutions of KOH, NaOH, LiOH, MeOK and EtONa in heterogeneous phase and under different conditions. In agreement with thermodynamic calculations, FT-IR and electronic spectra (by the 1st derivative of the absorption curve) provide clear evidence about the formation of long polyyne segments (acetylenic carbyne domains) conjugated with residual double bonds. More in detail, FT-IR spectra show a neat absorption band at 2180–2190 cm–1 due to triple bonds stretching while it is shown the strict analogy between electronic spectra recorded on the dehydrohalogenation products of chlorinated paraffins and the well known ene-polyynes like isomycomicyn and dodeca-2,10-diene-4,6,8-triyne.
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