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. 2001 Jun 18;40(12):2295-2298.
doi: 10.1002/1521-3773(20010618)40:12<2295::AID-ANIE2295>3.0.CO;2-W.

Matrix Isolation of Perfluorinated p-Benzyne

Hans H Wenk  1 , Andreas Balster  1 , Wolfram Sander  1 , David A Hrovat  2 , Weston T Borden  2
Affiliations

Matrix Isolation of Perfluorinated p-Benzyne

Hans H Wenk et al. Angew Chem Int Ed Engl. .

Abstract

As the first isolated derivative of 1,4-didehydrobenzene, 1,4-didehydro-2,3,5,6-tetrafluorobenzene (1) was generated from 1,4-diiodotetrafluorobenzene (2) by photolysis at 254 nm in a neon matrix at 3 K. The 4-iodo-2,3,5,6-tetrafluorophenyl radical 3 is formed as an intermediate in this reaction. Both 1 and 3 were characterized by their IR spectra. Compound 1 is photolabile and undergoes a photochemical retro-Bergman reaction to 1,3,4,6-tetrafluorohex-3-ene-1,5-diyne (4) upon broad-band UV irradiation (260-320 nm).

Keywords: 1,4-didehydrobenzene; IR spectroscopy; enediynes; matrix isolation.

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