OZONOLYSIS OF 1,1-DIFLUOROETHYLENE, TRIFLUOROETHYLENE, AND PERFLUOROETHYLENE: MECHANISM OF OZONIDE, EPOXIDE, AND CYCLOPROPANE FORMATION.

Article abstract of DOI:10.1021/ja00353a032

In this paper, preliminary studies with the ozonolyses of trifluoroethylene and 1,1-difluoroethylene are extended to low-temperature reaction conditions ( minus 78 and minus 95 C), and a complete product analysis is reported for both olefins. The isolation and identification of two previously unknown cyclopropane isomers, cis- and trans-1,1,2,3-tetrafluorocyclopropane, is discussed. The characterization of an unknown component in the trifluoroethylene ozonolyses as cis-1,2-difluoroethylene ozonide permits a determination of the cis-/trans-1,2-difluoroethylene ozonide ratio in these reactions. Results from aldehyde insertion experiments in the ozonolysis of CH//2 equals CF//2 and CF//2 equals CF//2 are related to the ozonide and epoxide mechanisms.