Synthesis of Ph3Sb(O2CR)2 Compounds with Unsaturated Carboxylic Acids and Use of Triphenylantimony Dicrotonate for the Production of Sb-Containing Polymers

The reactions of triphenylantimony with peroxides ROOH (R = t-Bu, H) and unsaturated carboxylic acids afforded triphenylantimony dicarboxylates Ph3Sb(O2CCH=CH2)2, Ph3Sb(O2CCMe=CH2)2, Ph3Sb(O2CCH=CHMe)2, Ph3Sb(O2CCH=CHPh)2, Ph3Sb(O2CCH=CHC6H4NO2-3)2, Ph3Sb(O2CCH=CHC4H3O)2, Ph3Sb(O2CCH=CHC6H4OMe-4)2, Ph3Sb(O2CCH=CHCH=CHMe)2, Ph3Sb(O2CCH2CH=CH2)2, and pTol3Sb(O2CCH=CHPh)2 in 35–86% yields. The structures of the obtained compounds were compared using the structural parameter τ (X-ray diffraction data) and the differences between νas(COO) and νs(COO) (IR spectroscopy data). For all the synthesized compounds, the antimony atom was found to have intermediate coordination between trigonal bipyramidal and tetragonal pyramidal and to be additionally coordinated to the carbonyl oxygen atoms. In triphenylantimony acrylate, methacrylate, crotonate, and sorbate, intermolecular interactions involving the C=C double bonds of the unsaturated carboxylate moieties of the neighboring molecules, arranged one above the other, were revealed. Antimony-containing transparent polymers, pol(methyl methacrylate) and polystyrene, which may be of practical value for the creation of new composite materials, were synthesized on the basis of triphenylantimony dicrotonate. The molecular weight characteristics, as well X-ray and UV light absorption by the obtained polymers were measured.