32117-38-7Relevant academic research and scientific papers
REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. II. NUCLEOPHILIC SUBSTITUTION IN NITROHALOGENO AND POLYFLUORINATED AROMATIC COMPOUNDS
Shtark, A. V.,Kizner, T. A.,Shteingarts, V. D.
, p. 2051 - 2056 (2007/10/02)
The possibility of aromatic nucleophilic substitution in liquid ammonia was investigated for the case of the reaction of p-nitrochlorobenzene, 2,4-dinitrochlorobenzene, hexafluorobenzene, bromopentafluorobenzene, pentafluorobenzene, and octafluoronaphthalene with a series of charged nucleophiles (potassium hydroxide and sulphite, alcoholates, sodium azide, thiophenolate, phenolate, and sulfide) at -70 to -33 deg C.It was shown that alkyl ethers of p-nitrophenol, phenyl p-nitrophenyl sulfide, 2,4-dinitrophenyl azide, polyfluorinaqted phenols, and their ethers can be obtained with good yields.Comparisons of the results with published data on the rate of the same reactions in other solvents shows that liquid ammonia is highly effective as a solvent for aromatic nucleophilic substitution reactions and in some cases makes it possible to avoid side processes.
