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The bicyclic amido‐substituted silicon(I) ring compound Si 4 {N(SiMe 3 )Mes} 4   2  (Mes=Mesityl=2,4,6‐Me 3 C 6 H 2 ) features enhanced zwitterionic character and different reactivity from the analogous compound Si 4 {N(SiMe 3 )Dipp} 4   1  (Dipp=2,6‐  i  Pr 2 C 6 H 3 ) due to the smaller mesityl substituents. In a reaction with the N‐heterocyclic carbene NHCMe4(1,3,4,5‐tetramethyl‐imidazol‐2‐ylidene), we observe adduct formation to give Si 4 {N(SiMe 3 )Mes} 4  ⋅ NHCMe4( 3 ). This adduct reacts further with the Lewis acid BH 3  to yield the Lewis acid–base complex Si 4 {N(SiMe 3 )Mes} 4  ⋅ NHCMe4 ⋅ BH 3  ( 4 ). Coordination of AlBr 3  to  2  leads to the adduct  5 . Calculated proton affinities and fluoride ion affinities reveal highly Lewis basic and very weak Lewis acidic character of the low‐valent silicon atoms in  1  and  2 . This is confirmed by protonation of  1  and  2  with Brookharts acid yielding  6  and  7 . Reaction with diphenylacetylene only occurs at 111 °C with  2  in toluene and is accompanied by fragmentation of  2  to afford the silacyclopropene  8  and the trisilanorbornadiene species  9 .

Reactivity of the Bicyclic Amido‐Substituted Silicon(I) Ring Compound Si 4 {N(SiMe 3 )Mes} 4 with FLP‐Type Character