Reactions of fluoro olefins
In competition for conjugation with an olefinic bond the phosphono group has a mote powerful electronwithdrawing effect than the trifluoromethyl group. The reaction of diethyl perfluoropropenylphosphonate with various nucleophilic reagents leads to products in which a fluorine atom in theβ -position relative to the phosphono group is replaced.
It was found that the electron-withdrawing effect of two trifluoromethyl groups is more powerful than the effect due to one phosphono group: in the reaction of diethyl perfluoroisobutenylphosphonate with nucleophilic reagents it is theα-fluorine atom that is replaced; in the case of diethyl α-hydrohexafluoroisobutenylphosphonate, addition products are formed with nucleophilic reagents, i.e. α-substituted-α, β-dihydrohexafluoroisobutylphosphonic esters.
KeywordsEster Diethyl Fluorine Trifluoromethyl Fluoro
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