Chlorinated Cyclic Carbonates, Glycolides and Ethers

Tetrachloro ethylidene carbonate (1), on treatment with hydrogen peroxide and base in the presence of a fluorescer, yields chemiluminescence with a maximum quantum yield of ca. 6.5 x 10 einsteinmole with emission from the fluorescer [1]  

This chemiluminescent reaction was suggested as occuring via ring opening of the cyclic carbonate group with subsequent ring closure to the peroxide (2). An alternative is formation of the diperoxy acid (3). Although a relationship to oxalyl chloride and peroxyoxalate chemiluminescence seems reasonable, details of the excitation step are not known. 

The perchloro-dioxolane (4), and the perchloro-l,4-benzodioxane (5) also produced hght on reaction with H2O2 and fluorescer, but with lower quantum yields. 

Similarly the chlorinated glycolides (6) have been reported to chemiluminesce under the conditions mentioned before [2]. 

The reaction of Martin s sulfurane [3], (7) which is used for the smooth dehydration of 1,2-diols to epoxides, with cumylhydroperoxide (8), hydrogen peroxide, or other hydroperoxides is chemiluminescent in the presence of DBA, or rubrene 

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