Synthesis and Reactivity of a Base-Free N-Heterocyclic Silanimine

Abstract

Reaction of the N-heterocyclic silylene (HCNDipp)2Si (1, Dipp = 2,6-iPr2C6H3) with the terphenyl azide ArN3 (Ar = 2,6-Mes2C6H3, Mes =2,4,6-Me3C6H2) in THF yielded the base-free silanimine (HCNDipp)2Si═NAr (2) with the almost linear Si═NC geometry in high yield. Reaction of 2 with sulfur and H2O resulted in the 1,3-addition of S2 to the C2N2Si ring and 1,2-addition of H2O to the Si═N bond, respectively.