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C,N-Chelated Organotin(IV) Azides: Synthesis, Structure and Use within the Click Chemistry.
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SYSNO ASEP 0461198 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title C,N-Chelated Organotin(IV) Azides: Synthesis, Structure and Use within the Click Chemistry. Author(s) Švec, P. (CZ)
Bartoš, K. (CZ)
Růžičková, Z. (CZ)
Cuřínová, Petra (UCHP-M) RID, SAI, ORCID
Dušek, L. (CZ)
Turek, J. (BE)
de Proft, F. (BE)
Růžička, A. (CZ)Source Title New Journal of Chemistry. - : Royal Society of Chemistry - ISSN 1144-0546
Roč. 40, č. 7 (2016), s. 5808-5817Number of pages 10 s. Language eng - English Country GB - United Kingdom Keywords organotin(IV)azides ; click chemistry ; chelation Subject RIV CC - Organic Chemistry Institutional support UCHP-M - RVO:67985858 UT WOS 000385869600023 EID SCOPUS 84978036115 DOI 10.1039/c5nj03187g Annotation A set of tri- and diorganotin(iv) azides bearing 2-(N,N-dimethylaminomethyl)phenyl as a C,N-chelating ligand (LCN) has been prepared and structurally characterized. Triorganotin(iv) azides of the type LCNR2SnN3 (R = n-Bu (1) and Ph (2)) and (LCN)2(n-Bu)SnN3 are monomeric both in solution and in the solid state. The central tin atom in these species is five-coordinated with distorted trigonal bipyramidal geometry. Diorganotin(iv) azides of the type LCNRSn(N3)2 (R = n-Bu and Ph) are monomeric with trigonal bipyramidal geometry around the tin atom as well. Finally, (LCN)2Sn(N3)2 contains a six-coordinated tin atom with heavily distorted octahedral geometry due to the presence of two LCN units. The potential use of selected organotin(iv) azides 1 and 2 as useful building blocks within click chemistry was investigated. The reactions of 1 and 2 with various nitriles resulted in the formation of corresponding triorganotin(iv) tetrazolides (i.e. κ-N1: LCN(n-Bu)2Sn(5-MeCN4), LCNPh2Sn(5-MeCN4), LCN(n-Bu)2Sn(5-Me2NCH2CN4), LCNPh2Sn(5-Me2NCH2CN4); and κ-N2: LCN(n-Bu)2Sn(5-t-BuCN4), LCNPh2Sn(5-t-BuCN4), LCN(n-Bu)2Sn(5-PhCN4), LCNPh2Sn(5-PhCN4)). Similarly, the reaction of 1 and 2 with cyclooctyne provided corresponding C,N-chelated di-n-butyl/diphenyltin(iv) κ-N1 4,5,6,7,8,9-hexahydrocycloocta[d][1,2,3]triazol-1-ides. All azido complexes and products of the [3+2] cycloaddition reactions were characterized by the combination of elemental analysis, mass spectrometry, IR spectroscopy, multinuclear NMR spectroscopy and, in the case of crystalline materials, XRD analysis. In addition, DFT calculations were carried out within the click chemistry reactions in order to corroborate the preferred formation of the respective tetrazolide regioisomer. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2017
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