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. 1998 Apr 20;37(7):955-958.
doi: 10.1002/(SICI)1521-3773(19980420)37:7<955::AID-ANIE955>3.0.CO;2-T.

p-Benzyne

Ralph Marquardt  1 , Andreas Balster  1 , Wolfram Sander  1 , Elfi Kraka  2 , Dieter Cremer  2 , J George Radziszewski  3
Affiliations

p-Benzyne

Ralph Marquardt et al. Angew Chem Int Ed Engl. .

Abstract

A noble gas matrix at low temperature was used to investigate the photochemical behavior of diacetyl terephthaloyl diperoxide and dipropionyl terephthaloyl diperoxide as well as 1,4-diiodobenzene. All three photoreactions formed small quantities of a compound with IR absorption bands at 725 and 980 cm-1 , which disappeared when the matrix was annealed. These bands correspond to the most intense of the calculated bands (B3LYP) for 1,4-didehydrobenzene (p-benzyne) (1). That decomposition of the peroxides in fact leads to 1 is confirmed by vapor-phase pyrolysis experiments in which (Z)-2 was obtained in high yield.

Keywords: Ab initio calculations; Density functional calculations; Matrix isolation; Photochemistry; Radicals.

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