C,N-Chelated Organotin(IV) Azides: Synthesis, Structure and Use within the Click Chemistry.

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F16%3A00461198" target="_blank" >RIV/67985858:_____/16:00461198 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1039/c5nj03187g" target="_blank" >http://dx.doi.org/10.1039/c5nj03187g</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c5nj03187g" target="_blank" >10.1039/c5nj03187g</a>

Result language

angličtina

Original language name

C,N-Chelated Organotin(IV) Azides: Synthesis, Structure and Use within the Click Chemistry.

Original language description

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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

—

Volume of the periodical

40

Issue of the periodical within the volume

7

Country of publishing house

GB - UNITED KINGDOM

Number of pages

10

Pages from-to

5808-5817

UT code for WoS article

000385869600023

EID of the result in the Scopus database

2-s2.0-84978036115