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Propargyl Fluoride and its Microwave Spectrum

Naturevolume 193page677 (1962) | Download Citation



ALTHOUGH propargyl halides have long been known, there appears to be no report of propargyl fluoride (3-fluoropropyne), FCH2C≡CH. This substance is of interest from the point of view of its chemical reactivity, and of its molecular structure, which is very suitable for spectroscopic study. We have found that propargyl fluoride can be made by the method, applied to certain other fluorides1, of treating the p-toluene sulphonate of the corresponding alcohol with potassium fluoride. Specimens boiling at approximately 15° C. (760 mm.) have been characterized as essentially pure by examination of their spectra. Infra-red bands establish the presence of the —C CH residue, while the CH2 and CF groupings give rise to bands closely resembling those which we have also found in the spectrum of fluoroacetonitrile, FCH2.CN. The CF stretching mode in propargyl fluoride yields a very strong band at 1,045 cm.−1, whereas the corresponding band in fluoroacetonitrile lies at 1,070 cm.−1. More detailed infra-red studies of these molecules are in progress in this laboratory.

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  1. Department of Chemistry, The University, Birmingham, 15

    • B. E. JOB
    •  & J. SHERIDAN


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