Journal of the American Chemical Society, Vol.138, No.33, 10421-10424, 2016
NHC-Stabilized Silicon-Carbon Mixed Cumulene
The NHC-stabilized silicon carbon mixed cumulene (Me3Si)(2)C=Si(IPr)=Si(IPr)=C(SiMe3)(2) (3, IPr = 1,3-diisopropyl-4,5-dimethyl-imidazol-2-ylidene) has been prepared by reaction of Ar(SiMe3)NK with the NHC-stabilized silene (Me3Si)(2)C=Si(SiMe3)Cl(IPr) (2) in toluene at low temperature via the elimination of trimethylsilyl and chloride groups from 2. X-ray crystal analysis of 3 indicated the formal C=Si=Si=C cumulene skeleton with the short Si Si double bond distance of 2.1896(10) angstrom. DFT calculations disclosed its zwitterionic character. Reaction of 3 with diphenylacetylene resulted in the formation of a silatriafulvene with an exocyclic NHC-stabilized silene moiety.