- Synthesis and characterization of dialkyl esters of 1,2,4,5-tetrazine-3,6- dicarboxylic acid
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Synthesis and characterization of a series of dialkyl esters of 1,2,4,5-tetrazine-3,6-dicarboxylic acid are reported. These compounds were prepared by a two-stage synthesis: re-esterification of dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate in the presence of aluminium triethoxide and subsequent dehydrogenation of dialkyl 1,4-dihydro-1,2,4,5- tetrazine-3,6-dicarboxylates. The structures of the prepared compounds were confirmed by NMR and mass spectra.
- Frebort, Stepan,Almonasy, Numan,Hrdina, Radim,Lycka, Antonin,Lisa, Miroslav,Holcapek, Michal
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- Structure and properties of nitrogen-rich 1,4-dicyanotetrazine, C4N6: A comparative study with related tetracyano electron acceptors
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The crystal structure, redox electrochemical stability, and reaction chemistry of 1,4-dicyanotetrazine (DCNT) has been experimentally characterized. These experimental results were rationalized by the results of theoretical calculations of the electronic structure, spin and charge distributions, electronic absorption spectra, and electron affinity and compared with the results for related the tetracyano electron acceptors tetracyanoethylene (TCNE), 7,7,8,8-tetracyano-p-quinodimethane (TCNQ), and 2,3,5,6-tetracyanopyrazine (TCNP). DCNT is made from the dehydration of 1,2,4,5-tetrazine-3,6-dicarboxamide, and because of the unusual deep-magenta color of the dicarboxamide in the solid state, its hydrogen-bonded layered structure, electronic structure, and electronic absorption spectra were determined. The magenta color is attributed to its absorptions at 532 nm (18 800 cm-1), and this corresponds to normalized chromaticity coordinates of x = 0.42 and y = 0.31 in the pink/red/orange part of the 1931 CIE chromaticity diagram. In contrast with previous reports, DCNT exhibits an irreversible one-electron reduction at -0.09 V vs SCE (MeCN), and reduced forms of DCNT have yet to be isolated and characterized. In addition, the reactions of DCNT with V(CO)6, FeII(C5Me5)2, and I- are discussed.
- Vo, Hoa-Lan,Arthur, Jordan L.,Capdevila-Cortada, Mar?al,Lapidus, Saul H.,Stephens, Peter W.,Novoa, Juan J.,Arif, Atta M.,Nagi, Ramneet K.,Bartl, Michael H.,Miller, Joel S.
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- Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach
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An additive-free chemoselective ligation of dual clickable building blocks is demonstrated. The challenge of balancing reactivity and stability was achieved by employing a small, electron-deficient tetrazine bearing an azido group and an enol ether functionalized cyclooctyne. The chemoselective sequence of strain-promoted azide-alkyne cycloaddition (SPAAC) and inverse-electron-demand Diels-Alder (IEDDA) reaction is demonstrated with a cholic acid derived triazide as a molecular surface model for layer-by-layer synthesis.
- Meinecke, Jannick,Koert, Ulrich
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supporting information
p. 7609 - 7612
(2019/10/02)
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