ChemInform Abstract: Reactions of Pentafluorophenylhydrazine and Some of Its N′‐Acyl Derivatives with Compounds Containing a Trichloromethyl Group in the Presence of Aluminum Chloride.

Abstract

The reactions of the title compound (I), the N′‐acyl derivatives (V) and the N,N‐bis‐pentafluorophenyl derivative (VII) with CCl4, PhCCl3 and C6F5CCl3 in the presence of AlCl3 are studied.

Polyfluoroaromatic compounds with a NCClR group—a reactive type of polyfluoroarene

“…Reaction of 1 with AlCl 3 and cis-1-pentafluorophenyl-2-fluorotetrachloropropene gives a 2:3 mixture of isomeric Z-and E-azadienes 67 with cis-and trans-orientations of halogen atoms relative to the C C bond. The structure of isomers 67 was confirmed not only by 19 F NMR data but also by hydrolysis of these compounds leading to amides, as would be expected for imidoyl chlorides. In the case of the E-isomer 67, the amide was isolated and characterized (compound 68E).…”

“…Hydrazonoylaryl chlorides 60 and 61 are the main products in the reactions of pentafluorophenylhydrazine (47) with benzotrichlorides 18 and 55, respectively, and AlCl 3 (Scheme 7) [19]. At room temperature the yields are 9 and 25%.…”

“…Low-basic hydrazines, for example, pentafluorophenylhydrazine (47) and p-nitrophenylhydrazine, react with carbon tetrachloride in the prsence of AlCl 3 , giving N-(aryl)hydrazonodichloro-methanes [19]. The reaction proceeds at two nitrogen atoms.…”

“…With carbon tetrachloride and AlCl 3 phenylhydrazine forms only a high melting stable complex. Final products of reactions of N-acyl derivatives of hydrazine 47 with carbon tetrachloride and AlCl 3 are 1-pentafluorophenyl derivatives of 1,3,4-oxadiazole-2-in-5-ones [19].…”

“…A general procedure for the synthesis of polyfluoroaromatic derivatives with a -N CClR group is based on reactions of low-basic aromatic amines or hydrazines with compounds of the general formula RCX 3 (X Cl or F) in the presence of AlCl 3 at moderate temperatures [17][18][19]. The same accessible starting amines are used as in the thermolysis described above.…”