caa a22 4500 475760298 CHVBK 20180406123549.0 cr unu---uuuuu 170329e20000301xx s 000 0 eng 10.1007/BF02494783 doi (NATIONALLICENCE)springer-10.1007/BF02494783 2-Phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics [Elektronische Daten] [M. Gurskii, D. Pershin, V. Ponomarev, I. Gridnev, O. Tok, Yu. Bubnov] 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 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). Kluwer Academic/Plenum Publishers, 2000 triallylborane nationallicence allylboron-acetylenic condensation nationallicence 1-boraadamantane compounds nationallicence amine complexes nationallicence hindered rotation nationallicence dynamic NMR nationallicence Gurskii M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Pershin D. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Ponomarev V. Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125820, Moscow, Russian Federation aut Gridnev I. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Tok O. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Bubnov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/3(2000-03-01), 499-502 1066-5285 49:3<499 2000 49 11172 https://doi.org/10.1007/BF02494783 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02494783 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Gurskii M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Pershin D. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Ponomarev V. Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125820, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Gridnev I. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Tok O. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Bubnov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/3(2000-03-01), 499-502 1066-5285 49:3<499 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer