Synthesis of triphenylantimony bis(phenylcarboranylacetate)

Full text of DOI:10.1134/S1070363210060319

ISSN 1070-3632, Russian Journal of General Chemistry, 2010, Vol. 80, No. 6, p. 1213. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © V.V. Sharutin, V.S. Senchurin, V.I. Bregadze, G.G. Zhigareva, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 6,
p. 1045.
LETTERS
TO THE EDITOR
Synthesis of Triphenylantimony Bis(phenylcarboranylacetate)
V. V. Sharutina, V. S. Senchurina, V. I. Bregadzeb, and G. G. Zhigarevab
a Blagoveshchensk State Pedagogical University, ul. Lenina 104, Blagoveshchensk, 675000 Russia
b Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia
Received December 7, 2009
DOI: 10.1134/S1070363210060319
Reaction of triphenylantimony with arylsulfonic
acid ArSO2OH (where Ar is a bulky organic sub-
stituent like α-naphthyl), which proceeds as oxidative
addition in the presence of hydrogen peroxide, is
known to afford triphenylantimony disulfonate in 25%
yield [1]. It was shown also that the yield of triphenyl-
antimony bis(arylsulfonates) increases in this reaction
to 94% at the use of an arylsulfonic acid containing
less bulky substituent.
Colorless crystals of compound I, well soluble in
organic solvents, precipitated from the rection mixture
over several hours.
Therefore, it is possible to conclude that in the
reaction of oxidative addition of such type the steric
factor affects the yield of the target product: more
bulky substituent in the initial acid leads to a decrease
in the end product yield.
In this work we studied the reaction of oxidative
addition of triphenylantimony to О–Н acid phenyl-
caboranylacetic acid involving a bulky phenylcar-
boranyl group. In this case the yield of the target reac-
tion product, triphenylantimony bis(phenylcarboranyl-
acetate) I, was shown to be 47%.
Triphenylantimony bis(phenylcarboranylacetate)
(I). To a solution of 0.40 g of triphenylantimony in
30 ml of diethyl ether were added 0.58 g of
phenylcarboranylacetic acid and 0.10 ml of 37% hyd-
rogen peroxide aqueous solution. The reaction mixture
was kept for 12 h at 20°С. After the solvent removal
the residue was recrystallized from hexane-benzene
mixture. Yield 0.46 g (47%), colorless crystals, mp
208°С. IR spectrum, ν, cm–1: 3063, 2578, 1653, 1480,
1436, 1347, 1206, 1072, 996, 950, 758, 733, 689, 665,
459. Found, %: С 47.04; Н 5.76. C34H49B20O4Sb.
Calculated, %: С 47.28; Н 5.68.
Ph
O
+ Ph3Sb + H2O2
2
CH2−C
OH
Ph
Ph
CH2−C
Ph
Sb
O
O
O
REFERENCES
C−CH2
O
1. Platonova, T.P., Candidate Sci. (Chem.) Dissertation,
Ph Ph
Vladivostok, 2002.
I
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