Abstract
1,1-Enediamines were prepared by reaction of N,N-dimethylacetamide dimethyl acetal, Me2NC(OMe)2CH3, with the cyclic amines piperidine, homopiperidine, and morpholine. The resulting unsymmetric 1-morpholino-1-(dimethylamino)ethene (1) and the symmetric 1,1-dipiperidinoethene (2a), 1,1-dihomopiperidinoethene (2b) and 1,1-dimorpholinoethene (2c) were reacted with [(THT)AuCl] (THT = tetrahydrothiophene), trans-PdCl2(NCPh)2 and B(C6F5)3, respectively, to afford a series of gold, palladium, and boron complexes 3a-f. The new complexes were fully characterized by NMR spectroscopy and X-ray diffraction analysis, revealing their analogy with N-heterocyclic olefins (NHO) by η1-coordination through highly polarized C−C double bonds. Chloride abstraction from (1,1-dimorpholinoethene)gold(I)-chloride (3c) with AgPF6 in presence of another equivalent of free ligand afforded bis(1,1-dimorpholinoethene)gold(I)-hexafluorophosphate (4) as the first homoleptic bis(1,1-enediamine) metal complex.
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