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

Article abstract of DOI:10.1021/ja00368a021

Thermolysis of 1,4-diphenyl-1,4-dioxa-2,3-benzopyrone (endoperoxide 1) in p-xylene solution generates chemiluminescence.Three products are formed from thermolysis of 1.The major product, trapped in 70percent yield by added maleic anhydride, is 1,4-diphenyl-2,3-benzodioxin (o-xylene peroxide 7).This peroxide eventually becomes o-dibenzoylbenzene 3 which is isolated from the reaction in 85percent yield.The two other products, 1,3-diphenylisobenzofuran (6) and phenyl o-benzoylbenzoate (4), are isolated in yields of ca. 2percent and 5percent, respectively.The observed chemiluminescence results from interaction of 7 with an added fluorescent activator or with the product 1,3-diphenylisobenzofuran according to the chemically initiated electron-exchange luminescence (CIEEL) mechanism.