| Autor: |
ANDO, Teiichi, ISHIHARA, Takashi, YANAGI, Yoshio |
| Jazyk: |
angličtina |
| Rok vydání: |
1982 |
| Zdroj: |
Memoirs of the Faculty of Engineering, Kyoto University. 44(2):249-256 |
| ISSN: |
0023-6063 |
| Popis: |
Each of the two geometrical isomers (1a and 1b) of 7-chloro-7-methylbicyclo-[4. 1. 0] heptane and the endo-methyl isomer (2a) of 7-bromo-7-methylbicyclo [4. 1. 0]-heptane were separately reduced with tributyltin hydride in a temperature range of 0 to 140°C, to give an isomeric mixture of 7-methylbicyclo[4. 1. 0]heptane (5). The endo : exo ratio in the product was 72±2 : 28±2, irrespective of the geometry of the starting halide. The reduction of 7-chloro-7-phenyIbicyclo [4. 1. 0] heptane (3) under similar conditions also proceeded nonstereospecifically to afford an isomeric mixture of 7-phenylbicyclo[4. 1. 0]heptane (6) with the endo : exo ratio of 90±2 : 10±2. The complete loss of stereospecificity in these reductions suggests that the intermediarily formed 7-methyl- and the 7-phenylbicyclo [4. 1. 0] hept-7-yl radicals are configurationally unstable and behave like a planar radical. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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