227103-03-9Relevant academic research and scientific papers
Crystalline (NN)C-M(NN) complexes: Synthesis, structure, bonding and lability [M = Si, Ge, Sn or Pb; (NN) = l, 2-(BuCH2N)2C6H4]
Gchrhus, Barbara,Hitchcock, Peter B.,Laeppert, Michael F.
, p. 3094 - 3099 (2000)
Each of the red-brown or red, isomorphous, crystalline adducts (NN)C-M(NN) [(NN) = l.l-CButCH2N2C6H4 and M = Si, Ge, Sn or Pb] has been obtained from the carbene (NN)C and the appropriate silylene, ge
N,N′-Bis(2,2-dimethylpropyl)benzimidazolin-2-ylidene: A stable nucleophilic carbene derived from benzimidazole
Hahn, F. Ekkehardt,Wittenbecher, Lars,Boese, Roland,Blaeser, Dieter
, p. 1931 - 1935 (1999)
N,N′-Dialkylated benzimidazol-2-thiones 6 can be prepared in a three-step procedure from o-phenylene-diamine. Thione 6a was reduced with sodium/potassium under desulfurization leading to carbene 4. Compound 4 is the first stable free carbene derived from benzimidazole. It exhibits the topology of an unsaturated carbene including a short C4-C5 bond. Its 13C NMR spectrum [δ(C2)=231.47] and selected structural parameters [angle N1-C2-N3 103.5(1)° and 104.2(1)°], however, correspond to those of saturated carbenes of the imidazolidin-2-ylidene type 3. The observation that the unsaturated carbene 4 behaves like a saturated imidazolidin-2-ylidene is corroborated by the tendency of the sterically less bulky N,N′-dialkylated thione 6b to yield the olefin 8 after reduction with Na/K. Carbene 4 can be coordinated to a W(CO)5 fragment yielding the complex 9, which contains a nonplanar carbene ring.
A crystalline carbene-silylene adduct 1,2-C6H4[N(R)]2C-Si[N(R)]2C6H4-1,2 (R = CH2Bu(t)); synthesis, structure and bonding in model compounds
Boesveld, W. Marco,Gehrhus, Barbara,Hitchcock, Peter B.,Lappert, Michael F.,Von Rague Schleyer, Paul
, p. 755 - 756 (2007/10/03)
The red-brown, crystalline carbene-silylene adduct, 1,2-C6H4[N(R)]2C-Si[N(R)]2C6H4-1,2 (R = CH2Bu(t))4, was obtained from its factors, the carbene 3 and silylene 1, or from Ni{C[N(R)]2(C)6H4-1,2}2 and 1; the X-ray structure of 4 shows a long C-Si bond [2.162(5) A] and NMR spectral data indicate significant C+-Si- bond polarity, features consistent with DFT calculations at the B3LYP/6-311+G** level on [(CH)2(NH)2]C-Si[(NH)2(CH)2], (H2N)2C-Si(NH2)2 or even [(CH)2(NH)2]C-SiH2 and (H2N)2C-SiH2, but not H2C = Si(NH2)2 or H2C = Si[(NH)2(CH)2].
