31. Aromatic polyfluoro-compounds. Part I. The synthesis of aromatic polyfluoro-compounds from pentafluorobenzene

Abstract

An m. p. of 106-107" has been given 2O for the acid.

Pentafluorobenzaldehyde and its utilizing in organic synthesis

“…Pentafluorobenzaldehyde was first prepared in 1959 [1]. Nield et al described in this paper the preparation of penta- fluorobenzene (2), which was realized by dehydrofluorination of the industrial product, 1H:4H/2H:5H-, 1H:5H/2H:4H-, 1H:2H/ 4H:5H-octafluorocyclohexane.…”

Ullmann Reaction Optimization within Bitolyl and Decafluorobiphenyl Synthesis

“…Noteworthy, in case of iodopentafluorobenzene the last approach leads to quantitative course (according to GC data) of the reaction 29,31 . This method is difficult to be scaled due to high cost of nickel iodide and aryl iodide and the use of fire-hazardous lithium and dimethoxyethane.…”

“…Using bromopentafluorobenzene under the same conditions substantially increase product output [27][28][29] (from 87% to 91%), yet replacing copper with activated nickel 30 , produced by reducing nickel bromide or nickel iodide with lithium naphthalede, is unsuccessful (37-49%).…”

Nucleophilic substitution in tris(pentafluorophenyl)phosphine

“…Studies of nucleophilic attack on pentafluorobenzene and its derivatives C6F5X (14)(15)(16)(17)(18)(19) show that the fluorine para to the hydrogen or other substituent X is most readily substituted (e.g., X =H, Me, SMe, NMe,) but meta substitution is possible (X = NH-, 0 -) . Burdon (20) and Epiotis and Cherry (21) have explained these observations on both qualitative and on a MO basis.…”