Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs

Winkelhaus D, Neumann B, Stammler H-G, Berger R, Vishnevskiy Y, Mitzel NW (2012)
Chemistry 18(30): 9312-9320.

Journal Article | Published | English

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Abstract
The reaction of (C6F5)2BH (1) with N,N-dimethylallylamine (2), N,N-diethylallylamine (3) and 1-allylpiperidine (4) afforded the five-membered ring systems (C6F5)2B(CH2)3NR2 (R=Me (5), Et (6)) and (C6F5)2B(CH2)3N(CH2)5 (7) with an intramolecular dative B?N bond. A different product was obtained from the reaction of (C6F5)2BH (1) with N,N-diisopropylallylamine (8), which afforded the seven-membered ring system (C6F5)2B(CH2)3N(iPr)CH(Me)CH2 (9) under extrusion of dihydrogen. All compounds were characterised by elemental analysis, NMR spectroscopy and single-crystal X-ray diffraction experiments. Density functional theory (DFT) studies were performed to rationalise the different reaction mechanism for the formation of products 6 and 9. The bonding situation of compound 9 was analysed in terms of its electron density topology to describe the delocalised nature of a borane enamine adduct.
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Winkelhaus D, Neumann B, Stammler H-G, Berger R, Vishnevskiy Y, Mitzel NW. Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs. Chemistry. 2012;18(30):9312-9320.
Winkelhaus, D., Neumann, B., Stammler, H. - G., Berger, R., Vishnevskiy, Y., & Mitzel, N. W. (2012). Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs. Chemistry, 18(30), 9312-9320.
Winkelhaus, D., Neumann, B., Stammler, H. - G., Berger, R., Vishnevskiy, Y., and Mitzel, N. W. (2012). Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs. Chemistry 18, 9312-9320.
Winkelhaus, D., et al., 2012. Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs. Chemistry, 18(30), p 9312-9320.
D. Winkelhaus, et al., “Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs”, Chemistry, vol. 18, 2012, pp. 9312-9320.
Winkelhaus, D., Neumann, B., Stammler, H.-G., Berger, R., Vishnevskiy, Y., Mitzel, N.W.: Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs. Chemistry. 18, 9312-9320 (2012).
Winkelhaus, Daniel, Neumann, Beate, Stammler, Hans-Georg, Berger, Raphael, Vishnevskiy, Yury, and Mitzel, Norbert W. “Inherent Stability Limits of Intramolecular Boron Nitrogen Lewis Acid-Base Pairs”. Chemistry 18.30 (2012): 9312-9320.
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