Addition of fluorine atoms to double and triple bonds

2 ADDITION OF FLUORINE ATOMS TO DOUBLE AND TRIPLE BONDS 

No absolute rate data exist for fluorine atom additions to olefins. This is not at all surprising in view of the tremendous experimental difficulties in carrying out reactions between fluorine and organic compounds of almost any sort. Rowland and co-workers [45] have been studying the interaction of fluorine atoms with a variety of compounds, however, and these include olefins. Relative rate data are given in Table 11 in a form such that the inter- and intramolecular reactivity of various unsaturated carbons is normalized against ethylene. The total reactivity is, of course, the summation of the positional reactivities of the individual carbons for any given compound. Rowland and co-workers [45a] have also measured the relative reactivity of the terminal versus the central carbon of propene towards fluorine atoms, and find the terminal position to be 1.35 times more reactive. 

Fluorine atom additions to fluorine-substituted ethylenes. Relative rate study [45] 

These reactions were carried out in a large excess of gaseous SFg, with thermalized fluorine-18 atoms produced from the F(n,2n) F nuclear reaction. The F reacts with the olefins by addition to produce excited adducts, which then interact with HI to produce stable products. 

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