2-phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics

M. E. Gurskii; D. G. Pershin; V. A. Ponomarev; I. D. Gridnev; O. L. Tok; Yu N. Bubnov

doi:10.1007/BF02494783

2-phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics

M. E. Gurskii, D. G. Pershin, V. A. Ponomarev, I. D. Gridnev, O. L. Tok, Yu N. Bubnov

Research output: Contribution to journal › Article › peer-review

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-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).

Original language	English
Pages (from-to)	499-502
Number of pages	4
Journal	Russian Chemical Bulletin
Volume	49
Issue number	3
DOIs	https://doi.org/10.1007/BF02494783
Publication status	Published - 2000 Jan 1
Externally published	Yes

Keywords

1-boraadamantane compounds
Allylhoron-acetylenic condensation
Amine complexes
Dynamic NMR
Hindered rotation
Triallylborane

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1007/BF02494783

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title = "2-phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics",

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-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).",

keywords = "1-boraadamantane compounds, Allylhoron-acetylenic condensation, Amine complexes, Dynamic NMR, Hindered rotation, Triallylborane",

author = "Gurskii, {M. E.} and Pershin, {D. G.} and Ponomarev, {V. A.} and Gridnev, {I. D.} and Tok, {O. L.} and Bubnov, {Yu N.}",

year = "2000",

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doi = "10.1007/BF02494783",

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volume = "49",

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journal = "Russian Chemical Bulletin",

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T1 - 2-phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics

AU - Gurskii, M. E.

AU - Pershin, D. G.

AU - Ponomarev, V. A.

AU - Gridnev, I. D.

AU - Tok, O. L.

AU - Bubnov, Yu N.

PY - 2000/1/1

Y1 - 2000/1/1

N2 - 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).

AB - 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).

KW - 1-boraadamantane compounds

KW - Allylhoron-acetylenic condensation

KW - Amine complexes

KW - Dynamic NMR

KW - Hindered rotation

KW - Triallylborane

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