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Matrix Isolation of Perfluorinated p ‐Benzyne
Author(s) -
Wenk Hans H.,
Balster Andreas,
Sander Wolfram,
Hrovat David A.,
Borden Weston T.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010618)40:12<2295::aid-anie2295>3.0.co;2-w
Subject(s) - matrix isolation , aryne , chemistry , photodissociation , photochemistry , derivative (finance) , matrix (chemical analysis) , irradiation , medicinal chemistry , infrared spectroscopy , organic chemistry , physics , chromatography , nuclear physics , financial economics , economics
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).