OZONOLYSIS OF ETHYLENE, VINYL FLUORIDE, AND 1,2-DIFLUOROETHYLENE - ISOTOPIC LABELING EXPERIMENTS

The condensed phase, low-temperature ozonolyses of ethylene, vinyl fluoride, and 1,2-difluoroethylene were investigated. Five trapping experiments are reported involving mixtures of these alkenes with an added aldehyde (formaldehyde or formyl fluoride). Four experiments are discussed where cross ozonide formation could be followed involving an isotopically enriched alkene or two different alkenes. These results indicate that the various synthetic routes to vinyl fluoride ozonide are consistent with a Criegee cleavage mechanism. It is likely that vinyl fluoride, upon ozonolysis, cleaves predominantly to H2COO and HCOF, but that some production of HFCOO and H2CO also occurs. Isotopic data suggest that the small amounts of cis-1,2-difluorooxirane produced upon ozonolysis of C2H3F (neat) may arise from trace amounts of 1,2-C2H2F2 present initially or produced during the ozonolysis. © 1979, American Chemical Society. All rights reserved.