Tris(2-methoxy-5-chlorophenyl)antimony: Synthesis and Oxidative Addition Reactions
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(2-methoxy-5-chlorophenyl)antimony: Synthesis and Oxidative Addition Reactions V. V. Sharutina,* and O. K. Sharutinaa a National
Research South Ural State University, Chelyabinsk, 454080 Russia *e-mail: [email protected]
Received June 1, 2020; revised June 1, 2020; accepted June 15, 2020
Abstract—The reaction of 2-methoxy-5-chlorophenyllithium with SbCl3 (3 : 1) in diethyl ether has afforded tris(2methoxy-5-chlorophenyl)antimony, which has been crystallized from benzene as solvate. Treatment of the solvate with bromine in chloroform has led to the formation of tris(2-methoxy-5-chlorophenyl)antimony dibromide, which has been isolated from benzene as solvate as well. The product of a similar reaction with chlorine, tris(2-methoxy5-chlorophenyl)antimony dichloride, has been also obtained via oxidation of tris(2-methoxy-5-chlorophenyl)antimony with copper dichloride in acetone. The structural features of the obtained compounds have been established by means of single-crystal X-ray diffraction analysis. Keywords: tris(2-methoxy-5-chlorophenyl)antimony, tris(2-methoxy-5-chlorophenyl)antimony dibromide, tris(2methoxy-5-chlorophenyl)antimony dichloride, X-ray diffraction analysis
DOI: 10.1134/S1070363220100138 Aryl derivatives of antimony bearing phenyl and 4-methylphenyl ligands have been the most studied [1]. Vacant d-orbitals of antimony atom can form additional bonds with the ligands having potential coordinating sites, which leads to the increase in coordination number and affects the compound properties, including reactivity. Only a few of antimony aryl derivatives of antimony with such potential coordinating sites as nitrogen [2–9] or oxygen [10–19] in the phenyl substituents have been known. To analyse aryl compounds of highly coordinated antimony(III), we have synthesised tris(2-methoxy-5chlorophenyl)antimony for the first time. Its reactions with halogens were investigated, and structural features of the synthesized compounds were elucidated. Tris(2-methoxy-5-chlorophenyl)antimony 1 was obtained from 2-methoxy-5-chlorophenyl and SbCl3 (Scheme 1). The starting aryl compound of lithium was obtained via lithiation of p-chloroanisole with phenyllithium in ether via the method described elsewhere [13, 14]. The interaction of compound 1 with a solution of bromine in chloroform led to the formation of tris(2methoxy-5-chlorophenyl)antimony dibromide, isolated as (2-MeO-5-ClC6H3)3SbBr2·0.5PhH solvate 2 upon
recrystallization from benzene. Tris(2-methoxy-5chlorophenyl)stibium dichloride 3 was obtained via passing of chlorine through a solution of tris(2-methoxy5-chloropheyl)antimony 1 in chloroform or treatment of compounds 1 with copper(II) chloride in acetone. Trisorganylantimony and its dihalides are used as precursors in the synthesis of other organic antimony(V) compounds [20–22]. Compounds 1–3 were high-melting colorless crystalline substances, stable against air moisture and oxygen, readily soluble in aromatic hydrocarbons, tetrachloromethane, tetrahydrofuran, and chloroform. IR spectra of compounds 1–3 conta
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