The cyclic alkyl(amino) carbene (cAAC) 1 reacted with SiI4 in toluene, affording the cAAC-silicon tetraiodide complex [(cAAC(Me))SiI4] (2, cAAC(me) = :C(CH2)(CMe2)(2)NAr, Ar = 2,6-iPr(2)C(6)H(3)). It further reacted with two equivalents of KC8 in toluene at room temperature to afford the first cAAC-diiodosilylene [(cAAC(Me))SiI2] (3). DFT calculations show that the C-carbene-Si bond in 3 is formed by the donation of the lone pair of electrons on the C-carbene atom to the SiI2 moiety, while the pi-back-bonding of the lone pair of electrons on the Si atom to the C-carbene atom is negligible. The presence of the lone pair of electrons on the silicon atom in 3 is also evidenced by its reaction with N3SiMe3 to form the cAAC-silaimine complex [(cAAC(Me))Si(NSiMe3)I-2] (4). Compound 3 reacted with iiprme (:C{N(iPr)CMe}(2)) in n -hexane to form the NHC-cAAC-silyliumylidene iodide [cAAC(Me)(SiI)I-iPrMe]I (5), which was then reacted with two equivalents of KC8 in toluene to furnish [cAAC(Me)Si(I-iPrMe)] (6). The experimental and theoretical studies suggest that 6 can be described as a bent silaallene with a perturbed electronic structure, which can be attributed to the different donor acceptor properties of cAAC(Me) and I-iPMe. Compounds 3-6 were elucidated by NMR spectroscopy, X-ray crystallography, and theoretical studies.