New organosilanes based on N-methylpyrrole – Synthesis, structure and characterization

The organosilanes trimethoxy(N-methylpyrrol-2-yl)silane (1), dimethoxybis(N-methylpyrrol-2-yl)silane (2), methoxytris(N-methylpyrrol-2-yl)silane (3), and tetrakis(N-methylpyrrol-2-yl)silane (7) were synthesized by lithiation of N-methylpyrrole with n-BuLi/TMEDA and subsequent reaction of the appropriate metalated species with Si(OMe)4. N-Methylpyrrol-2-ylsilane (4), bis(N-methylpyrrol-2-yl)silane (5), and tris(N-methylpyrrol-2-yl)silane (6) were obtained by treatment of compound 1 with DIBAL-H (diisobutylaluminium hydride), and silanes 2 and 3 by reaction with LiAlH4. Compounds 1–7 were characterized by 1H, 13C, 29Si NMR, ATR-IR and Raman spectroscopy, EI and ESI mass spectrometry, elemental analysis and single crystal X-ray diffraction analysis (2, 3, and 5–7). The silicon–hydrogen bond lengths are 1.360(2), 1.320(18) Å (5) and 1.386(18) Å (6). All compounds are thermally stable in the solid state and do not decompose prior to evaporation. The silanes are stable at ambient conditions for several days (1 and 4) or even months (2, 3 and 5–7).