✦ LIBER ✦
Physico-chemical study of indole alkaloids models. VI. Relative thermodynamic stability of endo- and semi-cyclic olefins in the bicyclo[2,2,2] octane system
✍ Scribed by G. Van Binst; Y. Merck
- Publisher
- Elsevier Science
- Year
- 1967
- Tongue
- French
- Weight
- 127 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Xany alkaloids contain a aomi-cyclic double bond on a l-azabicyclo[2,2,2]octane system. In order to study the relative stability of such olefina, we have prepared ethylidenebicyclo[2,2,2]octane and 2-ethylbicyclo[2,2,2]oct-2-ene as model compounds Elnd measured the equilibrium constant betwaen them by acid catalysis. Starting from bicyclo[2,2,2]octanone we obtained in two steps a mixture of ethylidenebicyclo[2,2,2]octanQ and of 2-cthylbicyclo[2,2,2]act-2-eno (ratio 57/43) with an overall yield of 69 $.