Conclusions
-
1.
Unsymmetrical perfluoro- and ω-hydroperfluoro-2-ketones are cleaved by the action of aqueous NaOH with the formation of the polyfluoroalkane corresponding to the longest ketone substituent.
-
2.
The product composition in the haloform cleaveage of α-chlorofluoroketones is determined by the stability of the chlorine-containing carbanions under the reaction conditions.
Similar content being viewed by others
Literature cited
G. P. Brandlin and Y. T. McBugh, Advances in Fluorine Chemistry [Russian translation], Vols. 3–4, Khimiya, Leningrad (1970), p. 231.
A. A. Glazkov, A. V. Ignatenko, S. P. Krukovskii, and V. A. Ponomarenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1570 (1978).
US Patent No. 3,238,241 (1966); Ref. Zh. Khim., 15N76 (1967).
J. H. Prager and P. H. Ogden, J. Org. Chem.,33, 2100 (1968).
C. G. Krespan, J. Org. Chem.,43, 637 (1978).
R. A. Moore and R. Levine, J. Org. Chem.,29, 1883 (1964).
J. Hine and D. C. Duffey, J. Am. Chem. Soc.,81, 1131 (1959).
A. Ya. Zapevalov, I. P. Kolenko, and V. S. Plashkin, Zh. Vses. Khim. Obshch. im. D. I. Mendeleeva,11, 1622 (1975).
L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, I. P. Kolenko, and L. S. German, Izv. Akad. Nauk SSSR, Ser. Khim., 1434 (1983).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1114–1116, May, 1983.
Rights and permissions
About this article
Cite this article
Saloutina, L.V., Zapevalov, A.Y., Kodess, M.I. et al. Perfluoro- and polyfluorochloroketones in the haloform cleavage reaction. Russ Chem Bull 33, 1023–1025 (1984). https://doi.org/10.1007/BF01141717
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01141717