Crystal structure of 2-(2,6-diisopropylphenyl)-N,N-diethyl-3,3-dimethyl-2-azaspiro[4.5]decan-1-amine: a diethylamine adduct of a cyclic(alkyl)(amino)carbene (CAAC)

The structure of the title compound, C27H46N2, at 93 K has monoclinic (P21/n) symmetry. The title compound was prepared by treatment of 2-(2,6-diisopropylbenzene)-3,3-dimethyl-2-azaspiro[4.5]dec-1-en-2-ium hydrogen dichloride with two equivalents of lithium diethylamide. Characterization of the title compound by single-crystal X-ray diffraction and 1H and 13C NMR spectroscopy is presented. Formation of the diethylamine adduct of the cyclic(alkyl)(amino)carbene (CAAC) was unexpected, as deprotonation using lithium diisopropylamide results in free CAAC formation.

Synthesis and Structural Characterization of a Series of Group 11 2,2-Dialkyl-1,3-dicyclohexylguanidinate Complexes

The addition of either lithium dimethylamide or lithium diethylamide to a tetrahydrofuran (THF) solution of 1,3-dicyclohexylcarbodiimide yielded THF adducts of lithium 2,2-dimethyl-1,3-dicyclohexylguandidinate (1) and lithium 2,2-diethyl-1,3-dicyclohexylguandidinate (2), respectively. One equivalent of either 1 or 2 was subsequently reacted with one equivalent of Group 11 halide (CuCl, AgBr, and AuCl) to generate oligonuclear complexes with the general formula {M[CyNC(NR2)NCy]}n where M, R, and n are respectively Cu, CH3, 2 (3); Cu, CH2CH3, 2 (4); Ag, CH3, 3 (5); Ag, CH2CH3, 3 (6); Au, CH3, 2 (7); and Au, CH2CH3, 2 (8). Compounds 1–8 were characterized by single-crystal X-ray diffraction. The bulk powders for all complexes were found to be in agreement with the crystal structures based on elemental analyses, Fourier transform infrared spectroscopy, and 1H, 13C, and 7Li NMR studies. The unique structural aspects of this family of Group 11 complexes are highlighted.