1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands

Weber L, Förster J, Stammler H-G, Neumann B (2011)
Zeitschrift für Anorganische und Allgemeine Chemie 637(12): 1711-1721.

Journal Article | Published | German

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Abstract
The reaction of the aminohaloboranes (Me(2)N)(R)BX (1) (a: R = Ph, X = Cl; b: R = Me, X = Br; c: R = iPr, X = Cl) with the di-Grignard reagent (BrMg)(2)CH(2) in ethyl ether/benzene mixtures afforded the diborylmethanes [(Me(2)N)(R)B](2)CH(2) (2) (a: R = Ph; b: R = Me; c: R = iPr), which were subsequently converted into the corresponding bis(chloroboryl)methanes [(Cl)(R)B](2)CH(2) (3) (a: R = Ph; b: R = Me; c: R = iPr). Base-assisted cyclocondensation of 3a-c with 1,2-diisopropylhydrazine afforded 1,2-diisopropyl-1,2-diaza-3,5-diorgano-3,5-diborolidines (4) (a: R = Ph; b: R = Me; c: R = iPr). Derivative 4a was deprotonated by potassium bis(trimethylsilyl) amide to give (1,2-diisopropyl-1,2-diaza-3,5-diphenyl-3,5-diborolidinyl)potassium (5). Attempts to introduce a halogen atom to the carbon bridge between the two boron atom by treating 5 with either iodine or 1,2-dibromoethane failed. Instead, bis(1,2-diisopropyl-1,2-diaza-3,5-diphenyl-3,5diborolidinyl) (C-C) (6) was formed. In contrast to this, C-silylation of the heterocycle to give 7 was effected by reaction of salt 5 with trimethylsilyl chloride. Similarly, treatment of HgCl(2) with two molar equivalents of 5 gave rise to the formation of bis(1,2-diisopropyl-1,2diaza-3,5-diphenyl-3,5-diborolidinyl)mercury (8). The novel compounds were characterized by elemental analyses and various spectroscopic methods ((1)H-, (11)B{(1)H}-, (13)C{(1)H} NMR, MS). The molecular structures of 4a and 6-8 were elucidated by X-ray diffraction analyses.
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Weber L, Förster J, Stammler H-G, Neumann B. 1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands. Zeitschrift für Anorganische und Allgemeine Chemie. 2011;637(12):1711-1721.
Weber, L., Förster, J., Stammler, H. - G., & Neumann, B. (2011). 1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands. Zeitschrift für Anorganische und Allgemeine Chemie, 637(12), 1711-1721.
Weber, L., Förster, J., Stammler, H. - G., and Neumann, B. (2011). 1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands. Zeitschrift für Anorganische und Allgemeine Chemie 637, 1711-1721.
Weber, L., et al., 2011. 1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands. Zeitschrift für Anorganische und Allgemeine Chemie, 637(12), p 1711-1721.
L. Weber, et al., “1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands”, Zeitschrift für Anorganische und Allgemeine Chemie, vol. 637, 2011, pp. 1711-1721.
Weber, L., Förster, J., Stammler, H.-G., Neumann, B.: 1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands. Zeitschrift für Anorganische und Allgemeine Chemie. 637, 1711-1721 (2011).
Weber, Lothar, Förster, Jan, Stammler, Hans-Georg, and Neumann, Beate. “1,2-Diaza-3,5-diborolidines CH(2)BR(1)-(NR(2))(2)-BR(1): Potential Precursors for Cyclic Diborylcarbene Ligands”. Zeitschrift für Anorganische und Allgemeine Chemie 637.12 (2011): 1711-1721.
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