288577-31-1Relevant academic research and scientific papers
2-phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics
Gurskii,Pershin,Ponomarev,Gridnev,Tok,Bubnov
, p. 499 - 502 (2000)
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-borabicyclo[3.3.1]non-6-ene (1) in 81% yield. Hydroboration of compound 1 with a solution of BH3 in THF yielded the tetrahydrofuran complex of 2-phenyl-1-boraadamantane (2). The reactions of trimethylamine or pyridine with compound 2 afforded the trimethylamine (3) or pyridine (4) complexes of 2-phenyl-1-boraadamantane, respectively. Hindered rotation about the C(2) - Ph bond in adduct 3 was observed by 1H and 13C NMR spectroscopy. The activation energy of this process is 58.6 kJ mol-1 (determined by 2D 1H - 1H EXSY spectroscopy).
