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 |
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container_issue | 29 |
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container_title | European Journal of Organic Chemistry |
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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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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)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200700192</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Betaines ; Carbenes ; Differential scanning calorimetry ; Thermogravimetric analysis</subject><ispartof>European Journal of Organic Chemistry, 2007-10, Vol.2007 (29), p.4909-4916</ispartof><rights>Copyright © 2007 WILEY‐VCH Verlag GmbH & Co. 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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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