Chemiluminescence of Organic Peroxides. Thermal Generation of an o-Xylylene Peroxide

Thermolysis of 1,4-diphenyl-1,4-dioxa-2,3-benzopyrone (endoperoxide 1) in p-xylene solution generates chemiluminescence. Two intermediate products are formed from thermolysis of 1. The major product, trapped in 70% yield by added maleic anhydride, is 1,4-diphenyl-2,3-benzodioxin (o-xylylene peroxide...

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Bibliographic Details
Main Authors: Smith,Jimmie P, Schrock,Alan K, Schuster,Gary B
Format: Report
Language:English
Subjects:
ABSORPTION SPECTRA
Atomic and Molecular Physics and Spectroscopy
BENZENE
BENZOATES
CHEMICAL DERIVATIVES
CHEMILUMINESCENCE
ELECTRON TRANSFER
EXCHANGE REACTIONS
EXCITATION
FLUORESCENCE
GAS CHROMATOGRAPHY
GROUND STATE
INFRARED SPECTROSCOPY
Organic Chemistry
ORGANIC COMPOUNDS
PEROXIDES
PHENYL RADICALS
RADIANT INTENSITY
REACTION KINETICS
THERMAL DEGRADATION
THERMAL PROPERTIES
ULTRAVIOLET SPECTROSCOPY
WUNR051616
XYLENES
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Summary:Thermolysis of 1,4-diphenyl-1,4-dioxa-2,3-benzopyrone (endoperoxide 1) in p-xylene solution generates chemiluminescence. Two intermediate products are formed from thermolysis of 1. The major product, trapped in 70% yield by added maleic anhydride, is 1,4-diphenyl-2,3-benzodioxin (o-xylylene peroxide 7). This peroxide becomes eventually o-dibenzoylbenzene 3 which is isolated from the reaction in 85% yield. The second intermediate is unidentified. It is formed in ca. 3% yield and apparently becomes eventually the other isolated product of the reaction phenyl-(o-benzoyl) benzoate (4). The chemiluminescence results from interaction of 7 with an added fluorescent activator or with the minor intermediate according to the chemically initiated electron-exchange luminescence (CIEEL) mechanism. (Author)