Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds

Tian X, Fröhlich R, Pape T, Mitzel NW (2005)
ORGANOMETALLICS 24(22): 5294-5298.

Journal Article | Published | English

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Abstract
Tenninally dilithiated tetramethylethylenediamine(TMEDA),LiCH2N(Me)CH2CH2N(Me)CH2Li (1), was prepared by transmetalation from Me3SnCH2N(Me)CH2CH2N(Me)CH2SnMe3 and n-BuLi. It was isolated as a highly air-sensitive white powder and was characterized by elemental analysis and by further transmetalation reactions. Compound 1 was used as a difunctional aminomethylating agent and reacted with R2MCl (R = Me, t-Bu; M = Al, Ga, In) to give the selective formation of 1,2,2,4,5,5-hexamethyl-1,4-diaza-2,5-dimetallabicyclo[2.2.2] octane (M = Al (2), Ga (3), In (4)) and 2,2,5,5-tetra-tert-butyl-1,4-dimethyl-1,4-diaza-2,5-dimetallabicyclo [2.2.2] octane (M = Al (5), Ga (6)) by simultaneous formation of two metal-carbon and two dative metal-nitrogen bonds accompanied by two ring closures. Compounds 2-6 were characterized by elemental analyses, by NMR spectroscopy (H-1, C-13, Al-27), and by crystal structure determinations. The 1,4-diazabicyclo [2.2.2] octane-like structure is favored over potential isomers containing three-membered rings and over polymeric aggregation. Despite the high steric demand of the tert-butyl groups, this conformation persists even in the case of 5 and 6.
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Tian X, Fröhlich R, Pape T, Mitzel NW. Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds. ORGANOMETALLICS. 2005;24(22):5294-5298.
Tian, X., Fröhlich, R., Pape, T., & Mitzel, N. W. (2005). Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds. ORGANOMETALLICS, 24(22), 5294-5298.
Tian, X., Fröhlich, R., Pape, T., and Mitzel, N. W. (2005). Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds. ORGANOMETALLICS 24, 5294-5298.
Tian, X., et al., 2005. Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds. ORGANOMETALLICS, 24(22), p 5294-5298.
X. Tian, et al., “Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds”, ORGANOMETALLICS, vol. 24, 2005, pp. 5294-5298.
Tian, X., Fröhlich, R., Pape, T., Mitzel, N.W.: Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds. ORGANOMETALLICS. 24, 5294-5298 (2005).
Tian, X, Fröhlich, R, Pape, T, and Mitzel, Norbert W. “Terminally dimetalated tetramethylethylenediamine (TMEDA) compounds”. ORGANOMETALLICS 24.22 (2005): 5294-5298.
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