Tetravalent Group 14 Derivatives of a Bulky Aminocarbazole

Stepwise metalation and metathesis reactions with a bulky aminocarbazole were conducted to prepare derivatives of tetravalent group 14 elements. These were regarded as putatively suitable precursors for the formation of doubly bonded group 14/group 15 molecules such as imino species. Starting from an N-aminocarbazole, deprotonation with benzyl potassium formed the corresponding solvent-free dimeric amide. Metathesis reactions with EBr4 (E=Si, Ge, Sn) afforded RN(H)EBr3. Deprotonation of RN(SiMe3)H with benzyl potassium afforded the solvent-free monomeric amide RN(SiMe3)K which was then treated with SiCl4, GeBr4 and SnI4. Both obtained series of compounds, RN(H)EBr3 and RN(SiMe3)EX3, were characterized by multinuclear NMR spectroscopy and SCXRD studies.