Dergiler / Turkish Journal of Chemistry / 2005 / Cilt: 29 - Sayı: 5
A New Approach to the Ring Opening Reactions of 2,7,7-Trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane
- Sayfa
- 531–538
- DOI
- —
Özet
The reaction of a-pinene and dibromocarbene produced a fairly unstable product, 2,7,7-trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane, from which 3-bromo-7,7-dimethyl-2-methylenebicyclo[4,1,1]oct-3-ene and 3-bromo-2,7,7-trimethylbicyclo [4,1,1]octa-2,4-diene were obtained in chloroform at room temperature and in various other media and conditions. Two new compounds, 3-bromo-2,7,7-trimethylbicyclo [4.1.1]oct-3-en-2-ol and 2-(4-bromo-5-methylcyclohepta-3,5-dien-1-yl) propan-2-ol, were observed in aqueous acetone in addition to the previous two. The stability and formation mechanism of the formed products are discussed
Abstract
The reaction of a-pinene and dibromocarbene produced a fairly unstable product, 2,7,7-trimethyl-3,3-dibromotricyclo[4.1.1.02,4]octane, from which 3-bromo-7,7-dimethyl-2-methylenebicyclo[4,1,1]oct-3-ene and 3-bromo-2,7,7-trimethylbicyclo [4,1,1]octa-2,4-diene were obtained in chloroform at room temperature and in various other media and conditions. Two new compounds, 3-bromo-2,7,7-trimethylbicyclo [4.1.1]oct-3-en-2-ol and 2-(4-bromo-5-methylcyclohepta-3,5-dien-1-yl) propan-2-ol, were observed in aqueous acetone in addition to the previous two. The stability and formation mechanism of the formed products are discussed