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 | |
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)