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Imidazolyl Alanes - Synthesis, Structures, and Reactivity Studies – Imidazolyl Alanes - Synthesis, Structures, and Reactivity Studies

Simon, Martin 1; Radius, Michael 1; Wagner, Hanna E. 1; Breher, Frank 1
1 Institut für Anorganische Chemie (AOC), Karlsruher Institut für Technologie (KIT)


Targeting the synthesis of Al/C based ambiphilic molecules, we investigated the dehydrohalogenation of a series of (benz)imidazole alane adducts. Depending on the steric bulk of the heterocycle, different dimeric products with various ring sizes were obtained. Dehydrohalogenation of the adduct of 1‐mesityl imidazole ($^{Mes}$Im) and 0.5 [tBu$_{2}$AlBr]$_{2}$ furnished the dimer 2, featuring a “classical” N‐heterocyclic carbene (NHC) and a mesoionic or “abnormal” NHC (aNHC) subunit within a single molecule. The dimer is bound loosely enough to allow thermally induced isomerization of 2 into the isomers 2$^{NHC}$ (all NHC) and 2$^{aNHC}$ (all aNHC). Dehydrohalogenation of the adduct of 1‐mesityl‐2‐methyl imidazole ($^{Mes}$Im$^{Me}$) and 0.5 [tBu$_{2}$AlBr]$_{2}$ (4) yielded the dimeric compound 5 consisting of two N‐heterocyclic olefin (NHO) subunits. Although these six‐ and eight‐membered heterocycles show no FLP‐type reactivity towards small molecules like H$_{2}$, CO or CO$_{2}$, we observed an ambiphilic behavior of the imidazolyl alanes during our studies. Salt metathesis reactions using $^{Mes}$Im resulted in the formation of 3, which can be viewed as tBu$_{2}$AlBr adduct of an Al/N ambiphile. ... mehr

Verlagsausgabe §
DOI: 10.5445/IR/1000125167
Veröffentlicht am 22.10.2020
DOI: 10.1002/ejic.202000174
Zitationen: 2
Web of Science
Zitationen: 2
Zitationen: 2
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Anorganische Chemie (AOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 05.2020
Sprache Englisch
Identifikator ISSN: 1434-1948
KITopen-ID: 1000125167
Erschienen in European journal of inorganic chemistry
Verlag Wiley-VCH Verlag
Band 2020
Heft 19
Seiten 1906–1914
Vorab online veröffentlicht am 29.04.2020
Nachgewiesen in Dimensions
Web of Science
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