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The unusual reactivity of the carbon-carbon double bond of tetrafluoroethylene brings about the participation of this versatile fluoroolefin in vinyl polymerization (1), cycloalkylation (2), and addition reactions (3). This paper reports further transformations of tetrafluoroethylene involving the addition of active hydrogen compounds, halogen, and analogous reactants.An important addition reaction is that of an alcohol with tetrafluoroethylene to obtain the corresponding alkyl ether. CF2=CF2 + ROH -> HCF2CF2ORA variety of ethers prepared in this way are listed in Table I in the Experimental Section. It is of interest that tetrachloroethylene does not react (3c) under similar conditions but chlorotrifluoroethylene does (3b, c, e).In some reactions of active hydrogen compounds with tetrafluoroethylene, for example, with amines, derivatives of difluoroacetic acid are obtained rather than the tetrafluoroethane compound. The mechanism of this unexpected transformation was revealed when it was found that reactions with sodium bisulfite gave both types of products, namely, sodium tetrafluoroethanesulfonate and sodium difluoroacetate.CF2=CF2 + NaHSOs -» HCF2CF2S03Na + HCF2COONaThe difluoroacetic acid derivative apparently results from the lability of the fluorine atoms -which are removed from the -carbon atom by hydrolysis.

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