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 journalArticlepeer-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 languageEnglish
Pages (from-to)499-502
Number of pages4
JournalRussian Chemical Bulletin
Volume49
Issue number3
DOIs
Publication statusPublished - 2000 Jan 1
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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