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Oxidation of Triarylantimony with Benzoyl Peroxide

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Abstract

Oxidation of triarylantimony Ar3Sb by peroxide benzoyl in benzene yielded relevant dibenzoates Ar3Sb[OC(O)Ph]2 [Ar = 4-FC6H4 (1), (4-F3C)C6H4 (2), (2-MeO)C6H4 (3), 4-BrC6H4 (4), 3‑MeC6H4 (5), 4-MeC6H4 (6), (4-Me2N)C6H4 (7), (2-MeO)(5-Br)C6H3] (8) up to 94%. Compounds 1−8 were identified using the IR spectroscopy and elemental analysis, and compounds 1 and 2 using the XRD analysis as well. According to the XRD data, crystals 1 consist of two types of crystallographically independent molecules (A and B), the geometrical parameters of which differ slightly from each other. Antimony atoms in 1 and 2 have trigonal pyramid coordination with benzoate ligands in axial positions. The Sb–C bond lengths are 2.042(11), 2.081(11), 2.143(9) Å for 1A, 2.091(10), 2.146(11), 2.162(9) Å for 1B, and 2.134(5), 2.135(4), 2.142(4) Å for 2. The Sb–O distances are 2.117(7), 2.128(8) Å for 1А, 2.117(7), 2.128(8) Å for 1В and 2.127(3), 2.133(3) Å for 2; however, metal atoms are also coordinated by carbonyl bidentate oxygen atoms carboxylate ligands (the distances Sb∙∙∙O=C vary in the intervals 2.669(9) −2.876(9) Å). The equatorial angles of CSbC are unequal: the largest angle is observed on the side of intramolecular contacts [103.6(5), 109.0(4), 147.2(4)° for 1A, 105.0(4), 108.1(4), 146.6(4)° for 1B, and 104.39 (17), 105.33(17), 150.21(16)° for 2]. The OSbO axial angles are 175.3(4), 176.0(4), and 175.10(10)°, respectively.

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ACKNOWLEDGMENTS

We express our gratitude to Prof. V.V. Sharutin for the X-ray diffraction analysis of crystals of compounds 1 and 2.

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  1. Kuban State University, 350040, Krasnodar, Russia

    V. V. Dotsenko

  2. South Ural State University, 454080, Chelyabinsk, Russia

    M. S. Golovin

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  1. V. V. Dotsenko
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Correspondence to V. V. Dotsenko.

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Translated by M. Chubarova

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Dotsenko, V.V., Golovin, M.S. Oxidation of Triarylantimony with Benzoyl Peroxide. rev. and adv. in chem. 12, 283–288 (2022). https://doi.org/10.1134/S2634827623700125

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