64101-18-4Relevant academic research and scientific papers
Reaction of N-Pentafluorophenylcarbonimidoyl Chloride with Aromatic Amines in the Presence of AlCl3
Petrova,Platonov
, p. 684 - 688 (2007/10/03)
Reactions of N-pentafluorophenylcarbonimidoyl chloride with aniline, N-methylaniline, N,N-dimethylaniline, and their polyfluorinated derivatives in the presence of AlCl3 (like Friedel-Crafts reactions) occur at the nitrogen atom of the amino gr
Reactions of polyfluoroaromatic imidoyl chloride derivatives with S-nucleophilic reagents
Petrova,Platonov,Shchegoleva,Maksimov,Haas,Schelvis,Lieb
, p. 13 - 25 (2007/10/03)
The interactions of N-pentafluorophenylcarbonimidoyl dichloride, N-pentafluorophenylbenzimidoyl chloride and N-pentafluorophenyl (C-pentafluorophenyl) imidoyl chloride with the S-nucleophilic reagents thiourea, sodium N,N-diethyldithiocarbamate, thiocarbonyl difluoride and bis(trifluoromethyl) trithiocarbonate in the presence of CsF or AgSCF3, or thiophenol and polyfluorinated thiophenols in the presence of anhydrous K2CO3, were studied. Reactions with charged S-nucleophiles and with S-nucleophiles in the presence of a base proceeded with preservation of the N=C multiple bond in the reaction products. By varying the reaction conditions in the case of N-pentafluorophenylcarbonimidoyl dichloride it was possible to substitute one or two chlorines and obtain mono- or di-thioimidates. When C6F5 or SC6F5 groups were present at the C atom of the N=C multiple bond, preferential substitution of the para-fluorine atom occurred. Semiempirical PM3 calculation data were used to explain the direction of these reactions. N-Pentafluorophenylcarbonimidoyl dichloride reacted with sodium N,N-diethyldithiocarbamate or thiourea to give pentafluorophenylisothiocyanate. Depending on the conditions of the reactions of polyfluorinated benzimidoyl chlorides with thiourea, N-pentafluorophenylthioamides and 2-aryl-4,5,6,7-tetrafluorobenzothiazoles were formed. An attempt to produce SCF3 derivatives from AgSCF3 was unsuccessful.
