220880-65-9Relevant academic research and scientific papers
Nucleophilic perfluoroalkylation of nitrones
Nelson, Derek W.,Easley, Regina A.,Pintea, Beniamin N. V.
, p. 25 - 28 (1999)
New methods for perfluoroalkylation of carbon-nitrogen double bonds have been developed. Addition of (trifluoromethyl)trimethylsilane (TMSCF3) to α,N-diarylnitrones produced α series of α-(trifluoromethyl)-N hydroxyl amines protected as their O-trimethylsilyl derivatives. An alternate procedure using pentafluoroethyllithium (F5C2L1) and chlorotrimethylsilane (TMSCI) afforded O-trimethylsilyl-α-(pentafluoroethyl)-N-hydroxyl amines.
α-(trifluoromethyl)amine derivatives via nucleophilic trifluoromethylation of nitrones
Nelson,Owens,Hiraldo
, p. 2572 - 2582 (2007/10/03)
(Trifluoromethyl)trimethylsilane (TMSCF3) reacts with nitrones to afford α-(trifluoromethyl)hydroxylamines protected as O-trimethylsilyl ethers. Potassium t-butoxide initiates the nucleophilic trifluoromethylation. The reaction works best with α,N-diaryl nitrones, and the conditions are compatible with a range of substituents on the aryl groups. Acidic deprotection of the nitrone/TMSCF3 adducts generates α-(trifluoromethyl)hydroxylamines. Catalytic hydrogenation of the adducts produces α-(trifluoromethyl)amines. Nitrone/TMSCF3 adducts with strong electron-withdrawing groups on the α-aryl ring or heterocyclic α-aryl groups undergo an elimination/addition sequence to generate α, α-bis(trifluoromethyl)amines. Nitrones with alkyl groups bound directly to the 1,3-dipolar moiety fail to react with TMSCF3, but trifluoromethylation of β,γ-unsaturated nitrones followed by reduction of the double bond can circumvent this limitation.
