2-Phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics |
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Authors: | M E Gurskii D G Pershin V A Ponomarev I D Gridnev O L Tok Yu N Bubnov |
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Institution: | (1) Moscow M. V. Lomonosov State University, Moscow, 199992, Russia; |
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Abstract: | The reaction of triallylborane with 3-phenylprop-1-yne at 135–140 °C followed by treatment of the reaction mixture with MeOH afforded 7-benzyl-3-methoxy-3-borabicyclo3.3.1]non-6-ene (1) in 81% yield. Hydroboration of compound1 with a solution of BH3 in THF yielded the tetrahydrofuran complex of 2-phenyl-1-boraadamantane (2). The reactions of trimethylamine or pyridine with compound2 afforded the trimethylamine (3) or pyridine (4) complexes of 2-phenyl-1-boraadamantane. respectively. Hindered rotation about the C(2)−Ph bond in adduct3 was observed by1H and13C NMR spectroscopy. The activation energy of this process is 58.6 kJ mol−1 (determined by 2D1H−1H EXSY spectroscopy). |
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