Double N–H bond activation of N,N′-bis-substituted hydrazines with stable N-heterocyclic silylene

Abstract

The reaction of N-heterocyclic silylene (NHSi) L [L = CH{(CCH₂)(CMe)(2,6-iPr₂C₆H₃N)₂}Si] with benzoylhydrazine, 1,2-dicarbethoxyhydrazine, 1,2-diacetylhydrazine and 1,2-bis(tert-butoxycarbonyl)hydrazine in 1 : 1 molar ratio resulted in compounds 1–4 with an almost quantitative yield and five coordinate silicon atoms. Compounds 1–4 were formed by double N–H bond activation by deliberate selection of N,N′-bis-substituted hydrazine compounds bearing the –C(O)NHNH– unit. Compounds 1–4 were characterized by NMR spectroscopy, EI-MS and elemental analysis. The molecular structures of compounds 1–3 were unambiguously established by single crystal X-ray structural analysis.