N-Heterocyclic Carbenes of 5-Haloindazoles Generated by Decarboxylation of 5-Haloindazolium-3-carboxylates

Syntheses and properties of 5‐fluoro‐, chloro‐ bromo‐, and iodo‐substituted 1,2‐dimethyl indazolium‐3‐carboxylates as new representatives of pseudo‐cross‐conjugated heterocyclic mesomeric betaines are described, and results of an X‐ray single crystal analysis of the nonhalogenated parent compound ar...

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Veröffentlicht in:European Journal of Organic Chemistry 2007-10, Vol.2007 (29), p.4909-4916
Hauptverfasser: Schmidt, Andreas, Snovydovych, Bohdan, Habeck, Tobias, Dröttboom, Petra, Gjikaj, Mimoza, Adam, Arnold
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container_end_page 4916
container_issue 29
container_start_page 4909
container_title European Journal of Organic Chemistry
container_volume 2007
creator Schmidt, Andreas
Snovydovych, Bohdan
Habeck, Tobias
Dröttboom, Petra
Gjikaj, Mimoza
Adam, Arnold
description Syntheses and properties of 5‐fluoro‐, chloro‐ bromo‐, and iodo‐substituted 1,2‐dimethyl indazolium‐3‐carboxylates as new representatives of pseudo‐cross‐conjugated heterocyclic mesomeric betaines are described, and results of an X‐ray single crystal analysis of the nonhalogenated parent compound are presented. These betaines decarboxylate on heating to yield 5‐halo‐1,2‐dimethyl‐indazol‐3‐ylidenes, which can be trapped by protons, sulfur, and 2,4‐dichlorophenylisocyanate, respectively. The decarboxylation is studied by electrospray‐ionization mass spectrometry, NMR spectroscopy, thermogravimetric analysis, and differential scanning calorimetry. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
doi_str_mv 10.1002/ejoc.200700192
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subjects Betaines
Carbenes
Differential scanning calorimetry
Thermogravimetric analysis
title N-Heterocyclic Carbenes of 5-Haloindazoles Generated by Decarboxylation of 5-Haloindazolium-3-carboxylates
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