1,2-Dioxetanedione

1,2-dioxetane -3 ,4- dione

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1,2- Dioxetandion has been proposed as a reactive intermediate ( intermediate) of the chemiluminescent reaction with hydrogen peroxide of Oxalsäurearylestern ( peroxyoxalate chemiluminescence). However, the existence of the heterocyclic compound appears to be unsafe. As a chemical compound would be 1,2- dioxetanes and Dioxetandion to the class of organic peroxides, especially among the peroxylactones. The four-membered ring heterocycle can also be regarded as a cyclic oxide of carbon or as a dimer of carbon dioxide.

It has been postulated that the 1,2- Dioxetandion decomposes carbon dioxide in an exergonic reaction, two molecules. The energy to be transferred to the dye molecules ( fluorescent dyes ), so that the phenomenon of chemiluminescence occurs.

Further intermediate cascades were discussed for the energy transfer. The detection of 1,2- Dioxetandion in the gas phase by mass spectroscopic methods has been disputed. In solution, however, the compound was identified by 13C NMR spectroscopic study of the reaction of 13C -labeled oxalyl chloride with hydrogen peroxide.

Use

In light sticks are Dioxetandions - derivatives of oxalic acid used as starting materials for generating the postulated 1.2. Examples include bis ( 2,4,6- trichlorophenyl ) oxalate ( TCPO ) or bis (2,3- dinitrophenyl ) oxalate ( DNPO ). However, the starting material today most commonly commercially used is bis ( 2,4,5- trichlorophenyl -6- carbopentoxy ) oxalate ( CPPO ). All of these starting materials are acylating agents ( " reactive ester" ) and to react with the addition of hydrogen peroxide to two equivalents of (substituted) phenol and 1,2- Dioxetandion.