Russian Journal of General Chemistry, Vol. 71, No. 6, 2001, pp. 983 984. Translated from Zhurnal Obshchei Khimii, Vol. 71, No. 6, 2001,
pp. 1045 1046.
Original Russian Text Copyright
2001 by Sharutin, Sharutina, Osipov, Subacheva.
LETTERS
TO THE EDITOR
New Method for Preparing Aroxytetraaryl Derivatives
of Antimony
V. V. Sharutin, O. K. Sharutina, P. E. Osipov, and O. V. Subacheva
Blagoveshchensk State Pedagogical University, Blagoveshchensk, Russia
Received July 18, 2000
Aryl derivatives of antimony(V) of the general
formula Ar4SbX [X = Hlg, NO3, SCN, OSO2R,
OC(O)R] can be prepared by the reaction of pentaaryl-
antimony and a symmetrical antimony(V) derivative
Ar3SbX2 in an yield of up to 98% [1 4]. Analogos
reactions of pentaarylantimony with diaroxytriphenyl
derivatives of antimony are unknown. We have found
a new method for preparing tetraphenylantimony
aroxides by the reaction of pentaphenylantimony with
triphenylantimony diaroxides. By this method we
prepared phenoxytetraphenyl antimony (IIIa) and
%: C 64.86; H 4.75; Sb 23.35. C30H25O2Sb. Calcu-
lated, %: C 66.79; H 4.64, Sb 22.93.
Bis(p-nitrophenoxy)triphenylantimony (IIb).
To a mixture of 1.00 g of triphenylstibine and 0.79 g
of p-nitrophenol in 15 ml of ether, 0.28 ml of 30%
aqueous hydrogen peroxide was added. After 24 h,
yellow crystals formed and were filtered off and dried
to obtain 1.72 g (96%) of compound IIb, mp 176
177 C. Found, %: C 57.58; H 4.40; Sb 17.82. C30H25
O2Sb. Calculated, %: C 57.23; H 3.64, Sb 19.40.
(4-nitrophenoxy)tetraphenylantimony
IIIb
from
Phenoxytetraphenylantimony (IIIa). A mixture
of 1.00 g of pentaphenylantimony and 1.06 g of
diphenoxytriphenylantimony in 10 ml of toluene was
heated at 90 C for 2 h. The solvent was removed, and
the residue was crystallized from a 1:3 toluene
heptane mixture to obtain 2.05 g (99%) of compound
IIIa, mp 153 C. Published data [6]: mp 152 C.
pentaarylantimony I and triphenylantimony diaroxides
IIa, IIb in yields of 99% and 93%, respectively.
Ph5Sb + Ph3Sb(OAr)2
IIa, IIb
2Ph4SbOAr
I
IIIa, IIIb
Ar = C6H5 (a), C6H4(NO2)-4 (b).
(p-Nitrophenoxy)tetraphenylantimony (IIIb). A
mixture of 0.64 g of pentaphenylantimony and 0.79 g
of bis(p-nitrophenoxy)triphenylantimony in 10 ml
of toluene was heated for 2 h at 90 C. The solvent
was removed, and the residue was crystallized
from a 1:3 toluene heptane mixture to obtain
1.33 g (93%) of compound IIIb, mp 148 C. Pub-
lished data [7]: mp 148 C.
The reactions were carried out by heating the start-
ing materials in an aromatic hydrocarbon. The melting
points and IR spectra of the tetraphenylantimony
aroxides were consistent with those of samples pre-
pared from pentaphenylantimony and the correspond-
ing phenols [5 7]. The starting triphenylantimony
diaroxides were obtained by a procedure previously
used for the synthesis of triphenylantimony diacetate
[8]. Like in the latter synthesis, the oxidative addition
of phenol to triphenylstibine successfully occurred in
the presence of hydrogen peroxide in an yield of up
to 96%.
The IR spectra were recorded on a Hitachi-215
spectrometer in Vaseline oil.
REFERENCES
1. Sharutin, V.V., Senchurin, V.S., Sharutina, O.K.,
Pakusina, A.P., and Panova, L.P., Zh. Obshch. Khim.,
1996, vol. 66, no. 10, pp. 1755 1756.
Diphenoxytriphenylantimony (IIa). To a mixture
of 1.50 g of triphenylstibine and 0.80 g of phenol in
15 ml of ether, 0.42 ml of 30% aqueous hydrogen pe-
roxide was added. After 24 h, the colorless crystals
that formed were filtered off and dried to obtain 1.51
g (66%) of compound IIa, mp 149 150 C. Found,
2. Sharutin, V.V., Sharutina, O.K., Panova, L.P., and
Bel’skii, V.K., Zh. Obshch. Khim., 1997, vol. 67, no. 9,
pp. 1531 1535.
3. Sharutin, V.V., Sharutina, O.K., Pakusina, A.P., and
1070-3632/01/7106-0983$25.00 2001 MAIK Nauka/Interperiodica
Sharutin
