N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives

Tian X, Woski M, Lustig C, Pape T, Fröhlich R, Le Van D, Bergander K, Mitzel NW (2005)
ORGANOMETALLICS 24(1): 82-88.

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Abstract
N,N-Diisopropylaminomethyllithium (1) was prepared by transmetalation from (Me3SnCH2NPr2)-Pr-i and n-BuLi. It was characterized by NMR spectroscopy (H-1, C-13, Li-7). Compound 1 crystallizes as a hexamer ((LiCH2NPr2)-Pr-i)(6) and allowed the determination of the first solvent-free structure of an alpha-lithiated amine. It contains a Li-6 core (distorted octahedron) 6-fold capped by (CH2NPr2)-Pr-i units. 1 is very sensitive to air-oxidation. A partially [(LiCH2NiPr2)(4)-(LiOCH2NiPr2)(2) (2)] and a completely oxidized [((LiOCH2NPr2)-Pr-i)(6) (3)] cluster compound could be isolated. 2 and 3 were characterized by multinuclear NMR spectroscopy and by single-crystal X-ray diffraction. The results show that the hexameric structure is retained upon partial or complete oxidation. 1 was used as aminomethylating agent and reacted with Me2AlCl and Me2GaCl to give the aminomethylaluminum and -gallium compounds ((Me2MCH2NPr2)-Pr-i)(2) (M = Al, Ga), which are dimers containing six-membered rings. They were characterized by elemental analyses, NMR spectroscopy, and crystal structure determinations. They are present as dimers containing six-membered M2C2N2 rings in solution and in the solid state.
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Tian X, Woski M, Lustig C, et al. N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives. ORGANOMETALLICS. 2005;24(1):82-88.
Tian, X., Woski, M., Lustig, C., Pape, T., Fröhlich, R., Le Van, D., Bergander, K., et al. (2005). N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives. ORGANOMETALLICS, 24(1), 82-88.
Tian, X., Woski, M., Lustig, C., Pape, T., Fröhlich, R., Le Van, D., Bergander, K., and Mitzel, N. W. (2005). N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives. ORGANOMETALLICS 24, 82-88.
Tian, X., et al., 2005. N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives. ORGANOMETALLICS, 24(1), p 82-88.
X. Tian, et al., “N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives”, ORGANOMETALLICS, vol. 24, 2005, pp. 82-88.
Tian, X., Woski, M., Lustig, C., Pape, T., Fröhlich, R., Le Van, D., Bergander, K., Mitzel, N.W.: N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives. ORGANOMETALLICS. 24, 82-88 (2005).
Tian, X, Woski, M, Lustig, C, Pape, T, Fröhlich, R, Le Van, D, Bergander, K, and Mitzel, Norbert W. “N,N-diisopropylaminomethyllithium: Synthesis, oxidative degradation, and organoaluminum and -gallium derivatives”. ORGANOMETALLICS 24.1 (2005): 82-88.
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