Russian Journal of General Chemistry, Vol. 73, No. 8, 2003, p. 1322. Translated from Zhurnal Obshchei Khimii, Vol. 73, No. 8, 2003, p. 1398.
Original Russian Text Copyright
2003 by Sharutin, Senchurin, Petrov, Sharutina.
LETTERS
TO THE EDITOR
Reactions of Pentaphenylantimony and Pentaphehylphosphorus
with Arylmercury Chlorides
V. V. Sharutin, V. S. Senchurin, B. I. Petrov, and O. K. Sharutina
Blagoveshchensk State Pedagogical University, Blagoveshchensk, Russia
Received September 6, 2002
Proceeding with research into arylating properties
of pentaphenyl derivatives of antimony and phos-
phorus [1, 2], we have studied their reactions with
phenylmercury chloride and ferrocenylmercury
chloride.
Reaction of pentaphenylantimony with ferro-
cenylmercury chloride. A mixture of 0.34 g of penta-
phenylantimony, 0.28 g of ferrocenylmercury chlo-
ride, and 5 ml of toluene was heated at 100 C for 1 h.
The reaction mixture was cooled, the solvent was
removed, and the residue was extracted with hot water.
The extract was evaporated to obtain 0.30 g (96%) of
tetraphenylantimony chloride, mp 198 C. The water-
insoluble residue was chromatographed on Silica gel
L 5/40 (eluent petroleum ether) to obtain 0.11 g (92%)
of diphenylmercury, mp 122 C. The substance in-
soluble in petroleum ether was crystallized from
toluene to give 0.18 g (95%) of diferrocenylmercury,
mp 237 C {[published data [3]: mp 234 235 C
(decomp.)}.
It was shown that pentaphenylantimony reacts with
phenylmercury chloride (toluene, 100 C, 1 h) to give
diphenylmercury (78%) and tetraphenylantimony
chloride (87%).
Ph5Sb + PhHgCl
Ph2Hg + Ph4SbCl.
The reaction of pentaphenylantimony with ferro-
cenylmercury chloride (toluene, 100 C, 1 h) produces
tetraphenylantimony chloride (96%), diphenylmercury
(92%), and diferrocenylmercury 95%) by the follow-
ing scheme:
Reaction of pentaphenylphosphorus with phenyl-
mercury chloride. A mixture of 1.00 g of penta-
phenylphosphorus, 0.75 g of phenylmercury chloride,
and 6 ml of toluene was allowed to stand at room
temperature for 24 h. Crystals formed and were
filtered off, washed with petroleum ether, and dried
to obtain 0.81 g (90%) of tetraphenylphosphorus
chloride. The solvent was removed from the filtrate,
and the residue was chromatographed on Silica gel L
5/40 (eluent petroleum ether) to obtain 0.80 g (94%)
of diphenylmercury, mp 122 C.
C5H5FeC5H4HgCl + Ph5Sb
Ph4SbCl + C5H5FeC5H4Hg
1/2(C5H5FeC5H4)2Hg + 1/2Ph2Hg
Pentaphenylphosphorus phenylates phenylmercury
chloride under milder conditions (toluene, 20 C, 24 h).
Ph5P + PhHgCl
Ph2Hg + Ph4PCl
REFERENCES
The yields of diphenylmercury and tetraphenyl-
phosphorus chloride are 94 and 90%, respectively.
1. Sharutin, V.V., Sharutina, O.K., Senchurin, V.S., Ko-
valeva, T.A., Shcherbakov, V.I., and Gladyshev, E.N.,
Zh. Obshch. Khim., 2000, vol. 70, no. 1, pp. 69 70.
Reaction of diphenylantimony with phenyl-
mercury chloride. A mixture of 2.00 g of penta-
phenylantimony, 1.24 g of phenylmercury chloride,
and 10 ml of toluene was heated at 100 C for 1 h.
Crystals formed and were filtered off, washed with
petroleum ether, and dried to obtain 1.60 g (87%) of
tetraphenylantimony chloride, mp 198 C. The solvent
was removed from the filtrate, and the residue was
chromatographed on Silica gel L 5/40 (eluent petro-
leum ether) to obtain 1.10 g (78%) diphenylmercury,
mp 122 C (published data [3]: mp 122 C).
2. Sharutin, V.V., Sharutina, O.K., Senchurin, V.S., Ego-
rova, I.V., and Ivanenko, T.K., Abstracts of Papers,
II Mezhdunarodnyi simposium Khimiya i khimicheskoe
obrazovanie (II Int. Symp. Chemistry and Chemical
Education ), Vladivostok, 2000, pp. 197 198.
3. Makarova, L.G. and Nesmeyanov, A.N., Metody ele-
mentoorganicheskoi khimii. Rtut’ (Methods of Orga-
noelement Chemistry. Mercury), Moscow: Nauka,
1965.
1070-3632/03/7308-1322$25.00 2003 MAIK Nauka/Interperiodica
Sharutin
