TY - JOUR
T1 - Experimental and computational studies of trifluoromethylation of aromatic amines by the system trifluoroiodomethane‐zinc‐sulfur dioxide
AU - Strekowski, Lucjan
AU - Hojjat, Maryam
AU - Patterson, Steven E.
AU - Kiselyov, Alexander S.
PY - 1994
Y1 - 1994
N2 - Several trifluoromethyl‐substituted aromatic and heteroaromatic amines have been obtained by the reactions of the corresponding amines with the title reagent system. Computational results provide rationalization for the observed regioselectivities and support a mechanism in which the electrophilic trifluoromethyl radicals interact with the aromatic ring at the sites with the greatest electron density of the HOMO orbitals, and then the resultant adducts are oxidized to cations. The products obtained are potential building blocks for a number of heterocyclic systems.
AB - Several trifluoromethyl‐substituted aromatic and heteroaromatic amines have been obtained by the reactions of the corresponding amines with the title reagent system. Computational results provide rationalization for the observed regioselectivities and support a mechanism in which the electrophilic trifluoromethyl radicals interact with the aromatic ring at the sites with the greatest electron density of the HOMO orbitals, and then the resultant adducts are oxidized to cations. The products obtained are potential building blocks for a number of heterocyclic systems.
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U2 - 10.1002/jhet.5570310619
DO - 10.1002/jhet.5570310619
M3 - Article
AN - SCOPUS:84993917416
SN - 0022-152X
VL - 31
SP - 1413
EP - 1416
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 6
ER -