The reactivity of trifluoromethylated styrenes
Mechanistic study of multi-step nucleophilic substitution for trifluoromethylated styrenes
Scheme 2
We have shown that the direction of transformations depends dramatically on the nature of aromatic substituent of initial substrate: styrenes bearing an electron-withdrawing group are converted into trifluoromethy-lated enamines (secondary amines) and/or azomethines (primary amines) or heterocycles (binucleophiles) while their analogs bearing electron-donor group in benzene ring give unexpected products of nucleophilic C–F bond cleavage (primary or secondary amines) or fragmentation (binucleophiles) (Scheme 2).
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