Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles

Weber L, Dobbert E, Rausch A, Stammler H-G, Neumann B (1999)
Zeitschrift für Naturforschung. B, Journal of Chemical Sciences 54(3): 363-371.

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Synthese, Struktur und Reaktivität von 2-Amino- und 2-Imino-2,3-dihydro-1H-1,3,2-diazaborolen
Abstract
The 2-halo-2,3-dihydro-1H-1,3,2-diazaboroles RN-CH=CH-N(R)BX (1a': R = tBu, X = Br; 1b: R = 2,6-Me2C6H3; X = 1) were converted into the 2-amino-2,3-dihydro-1H-1,3,2-diazaboroles RN-CH=CH-N(R)B-NH2 (2a: R = tBu; 2b: 2,6-Me2C6H3) by treatment with dry gaseous ammonia. Similarly reaction of 1a' with 2,6-dimethylaniline or tBuNH(2) afforded the corresponding derivates tBuN-CH=CN-N(tBu)wBNHR(1) (3; R-1 = 2,6-Me2C6H3; 4; R-1 = tBu). The treatment of 1a' with the ethylene diamine adduct of lithium acetylide led to the formation of [tBuN-CH=CN-N(tBu)BN(H)CH2](2) (5). Lithiation of 2a and subsequent silylation gave 6 (R-1 = SiMe3), which was transformed to the diborolylamine [tBuN-CH=CH-N(tBu)B](2)NH (7) upon exposure to 1a'. Borolylketimine tBuN-CH=CH-N(tBu)B-N=CPh2 (8) and borolylcarbodiimide tBuN-CH=CHN(tBu)B-N=C=N-SiMe3 (9) resulted from 1a' and Ph2C=NSiMe3 or Me3SiN=C=NSiMe3, respectively. All the new compounds were characterized by elemental analyses as well as spectroscopic data (IR, H-1, B-11, C-13 NMR, MS). Heterocycle 5 was also subjected to an X-ray diffraction analysis.
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Weber L, Dobbert E, Rausch A, Stammler H-G, Neumann B. Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles. Zeitschrift für Naturforschung. B, Journal of Chemical Sciences. 1999;54(3):363-371.
Weber, L., Dobbert, E., Rausch, A., Stammler, H. - G., & Neumann, B. (1999). Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles. Zeitschrift für Naturforschung. B, Journal of Chemical Sciences, 54(3), 363-371.
Weber, L., Dobbert, E., Rausch, A., Stammler, H. - G., and Neumann, B. (1999). Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles. Zeitschrift für Naturforschung. B, Journal of Chemical Sciences 54, 363-371.
Weber, L., et al., 1999. Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles. Zeitschrift für Naturforschung. B, Journal of Chemical Sciences, 54(3), p 363-371.
L. Weber, et al., “Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles”, Zeitschrift für Naturforschung. B, Journal of Chemical Sciences, vol. 54, 1999, pp. 363-371.
Weber, L., Dobbert, E., Rausch, A., Stammler, H.-G., Neumann, B.: Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles. Zeitschrift für Naturforschung. B, Journal of Chemical Sciences. 54, 363-371 (1999).
Weber, Lothar, Dobbert, Eckhard, Rausch, Andreas, Stammler, Hans-Georg, and Neumann, Beate. “Synthesis, structure and reactivity of 2-amino- and 2-imino-2,3-dihydro-1H-1,3,2-diazaboroles”. Zeitschrift für Naturforschung. B, Journal of Chemical Sciences 54.3 (1999): 363-371.
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