128644-93-9Relevant academic research and scientific papers
Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks
Fuchigami, Toshio,Ichikawa,, Shinji
, p. 607 - 615 (2007/10/02)
Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH2Rf (Rf = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position α to the fluoromethyl (Rf) group, depending on the Rf and R groups.The effect of the Rf group on the promotion of the anodic α-methoxylation decreased in the order CF3, CHF2, and CH2F.This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the α-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines.The α-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds α to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.
CATIONIC POLAR CYCLOADDITION WITH ANODICALLY PREPARED α-TRI- and α-DIFLUOROMETHYLATED N,O-ACETALS: PREPARATION OF FLUOROMETHYLATED TETRA- and DIHYDROQUINOLINE DERIVATIVES
Fuchigami, Toshio,Ichikawa, Shinji,Kandeel, Zaghloul E.,Konno, Akinori,Nonaka, Tsutomu
, p. 415 - 417 (2007/10/02)
Anodically prepared α-tri- and α-difluoromethylated N,O-acetals readily underwent ++2> type polar cycloadditions with styrenes and phenylacetylene in the presence of a Lewis acid to provide the corresponding fluoromethylated tetra- and dihydr
