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Synthesis 1987; 1987(1): 42-43
DOI: 10.1055/s-1987-27835
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A Facile Synthesis of Perfluoro- and ω-Chloroperfluoro-1-pentafluorophenyl-1-alkynes

Yanchang Shen* , Weiming Qiu
  • *Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu, Shanghai, People's Republic of China
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Publication Date:
20 August 2002 (online)

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Perfluoro-1-pentafluorophenyl-1-alkynes and the corresponding ω-chloroperfluoro compounds are conveniently prepared by the following two-step sequence: Reaction of methylenetriphenylphosphorane with hexafluorobenzene followed by C-acylation of the resultant perfluorobenzylidenetriphenylphosphorane (without isolation) with perfluoroalkanoic anhydrides or ω-chloroperfluoroalkanoyl fluorides, respectively, to give α-perfluoroacyl [or α-(ω-chloroperfluoroacyl)]-perfluorobenzylidenetriphenylphosphoranes and pyrolysis of these latter compounds at 230-260°C/2 torr. The second step of the sequence represents an intramolecular Wittig reaction.

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