HYDROGENOLYSIS OF C-HALOGEN BOND IN POLYFLUOROAROMATIC COMPOUNDS
S. Igumnov, K. Merkulov. E. Igumnova, V. Don
Well-known methods of hydrogenolysis of C-F and C-C1 bonds in polyfluoroaromatic
compounds are based on the reduction by LiAlH4 or by hydrogen in the presence
of the noble metals [1,2]. Major preparative instrest represents the reduction
of C-C1 and C-Br bonds in pentafluorochlorobenzenes and pentafluorobromobenzene
by Zn/Cu couple in the hydrous N,N-DMF [3]. It was found that with the use
ofMg in methanol with addition ofN,N-DMF it becomes possible to reduce C-F
bond in hexafluorobenzene resulting in a yield up to 60 %.
As a continuation of these research it was found that NaBH4 in the polar
solvents may have wide application for the hydrogenolysis of C-F bond in
polyfluoroaromatic compounds. Thus reduction of polyhalotoluenes and benzenes
results in the mixture of the products with the total yield up to 90% with
the para-isomer prevalence. Ratio of the products depends on the chosen solvent
and on the reaction conditions.
Isomeric tetrafluorobenzenes along with
pentafluorobenzene are formed in the Ireaction of hexafluorobenzene with
NaBH4.
1) T-Schach, T. Papenfuhs (US 5.498.807 (Cl.507.127; CO 7 25/13), 1996)
2) J. Res.; NBS, 6 (1959) N 3, 119-122) R.E. Florin, W.J.Pummer, L. A. Wall.
3) Organic Chemistry, 1994, 30 (8) 1271-1275, V. E. Platonov, V. L. Krasnov.
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The Russian-Japanese "Fluorine seminar"was held in N.N. Vorozhtsov Novosibirsk Institute of Organic
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