O -Trimethylsilyl- N -phenylsulfonylacetimidate: Synthesis and Structure
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imethylsilyl-N-phenylsulfonylacetimidate: Synthesis and Structure A. Yu. Nikonova, I. V. Sterkhovaa,*, N. A. Kolyvanova, V. Yu. Serykha, and N. F. Lazarevaa a
Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences, Irkutsk, 664033 Russia *e-mail: [email protected] Received April 30, 2020; revised April 30, 2020; accepted May 11, 2020
Abstract—A method for silylation of N-acetylbenzenesulfonamide has been proposed. The structural features of the obtained O-trimethylsilyl-N-phenylsulfonylacetimidate have been studied by means of NMR and IR spectroscopy as well as single-crystal X-ray diffraction analysis. Keywords: N-acylaryl sulfonamides, O-trimethylsilyl-N-phenylsulfonylacetimidate, silylation, silicon-containing sulfonamides
DOI: 10.1134/S1070363220090091 Silylation of organic compounds is widely applied in organic and analytical chemistry as well as in materials science [1–4]. Trisorganylsilyl fragments are efficient protective groups blocking the O-, N-, and S-reactive sites [3, 5]. The introduction of a silyl group in organic compounds alters their reactivity, improves the solubility in nonpolar solvents, and increases the volatility. Enhanced volatility allows the use of GLC and mass spectrometry for isolation and analysis of organic species [3, 6]. A series of organosilicon compounds [R1R2R3SiCl, R3SiNR2, and (Me3Si)2NH] have been used to introduce a silyl group in the compounds structure. О- or N-TMSand O,N-bis(TMS) derivatives of carboxylic and sulfonic acid amides and the related compounds are among the most efficient and convenient laboratory-scale donors of trimethylsilyl (TMS) groups [1–3, 7–9]. Siliconcontaining derivatives of N-acylarylsulfonamides RC(O)N(SiMe3)SO2Ar are of special interest, yet the data on these compounds have been scarce. To the best of our knowledge, they have been mentioned only in a few
reports [10–12]. This study aimed to elaborate a method of N-acetylbenzenesulfonamide 1 silylation and investigate the structure of the reaction products. N-Acetylbenzenesulfonamide 1 was prepared as described elsewhere [13]. Acylation of benzenesulfonamide with acetic anhydride in the presence of a catalytic amount of ZnCl2 occurred in bulk and afforded compound 1 in 90% yield (Scheme 1). N-Acetylbenzenesulfonamide reacted with trimethylchlorosilane in benzene medium, the yield of the silylation product 2 being 68%. The reaction occurred at room temperature in the presence of triethylamine as hydrogen chloride acceptor (Scheme 2). Structure of compound 2 was studied by means of IR and NMR spectroscopy as well as X-ray diffraction analysis. The crystal suitable for the latter were obtained via recrystallization. According to the X-ray diffraction analysis data, compound 2 in the crystal exists in the form of the O-silylated derivative 2b—O-trimethylsilyl-Nphenylsulfonylacetimidate. Molecular structure of
Scheme 1.
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NIKONOV et al. Scheme 2.
imidate 2b is shown in Fig. 1, and selected structural parameters of it are listed in Table 1. A s
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