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Routes to novel mono- and bis-tetrazole compounds: synthesis, spectroscopic and structural characterization

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Boland, Yves [UCL] Safin, Damir [UCL] Tinant, Bernard [UCL] Babashkina, Maria G. [UCL] Marchand-Brynaert, Jacqueline [UCL] Garcia, Yann [UCL]

Relatively easy-to-run synthetic routes to new mono- [1-(2-(4,5-dihydro-1H-imidazol-1-yl)ethyl)-1H-tetrazole (1) and 3-(2-(1H-tetrazol-1-yl)ethyl)oxazolidin-2-one (13)], and bis-tetrazole [N,N-bis(2-(1H-tetrazol-1-yl)ethyl)- formamide (2), bis(2-(1H-tetrazol-1-yl)ethyl)amine (3), N-(2-(1H-tetrazol-1-yl)ethyl)-N-(2-(2-(1H-tetrazol-1-yl)- ethylamino)ethyl)formamide (5), N1,N2-bis(2-(1H-tetrazol-1-yl)ethyl)ethane-1,2-diamine (6), N,N0-(2,20- azanediylbis(ethane-2,1-diyl))bis(N-(2-(1H-tetrazol-1-yl)ethyl)formamide) (8) and N1-(2-(1H-tetrazol-1-yl)ethyl)- N2-(2-(2-(1H-tetrazol-1-yl)ethylamino)ethyl)ethane-1,2-diamine (9)] ligands have been developed. 2 (whose crystal structure is described), 3, 5, 6, 8 and 9 are of particular interest as precursors for further functionalization due to the aldehyde and secondary amine functions, while 2, 5, 8 and 13 are potential synthons for the formation of ditopic ligands for metal–organic framework construction. Unexpected instability of Boc under basic and nucleophilic conditions at high temperature followed by fragmentation of tert-butyl 2-chloroethyl(2-(2-chloroethylamino)ethyl)carbamate (14) and tert-butyl 2,20-azanediylbis(ethane-2,1- diyl)bis(2-chloroethylcarbamate) (15) afforded 13, whose crystal structure is presented.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2013
Language Anglais
Journal information "New Journal of Chemistry" - Vol. 37, no./, p. 1174-1179 (2013)
Peer reviewed yes
Publisher Royal Society of Chemistry ((United Kingdom) Cambridge)
issn 1144-0546
e-issn 1369-9261
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Links
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Bibliographic reference Boland, Yves ; Safin, Damir ; Tinant, Bernard ; Babashkina, Maria G. ; Marchand-Brynaert, Jacqueline ; et. al. Routes to novel mono- and bis-tetrazole compounds: synthesis, spectroscopic and structural characterization. In: New Journal of Chemistry, Vol. 37, no./, p. 1174-1179 (2013)
Permanent URL http://hdl.handle.net/2078.1/126345