Stereochemistry of the nucleophilic ring-opening of activated bicyclo-[3.1.0]Hexanes.
โ Scribed by Daiei Tunemoto; Nobuhiko Araki; Kiyosi Kondo
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 222 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The nucleophilic ring-opening reaction of 2-oxobicycloI3.l.O]hexane-lcarboxylate (1) to afford an intermediate for the synthesis of prostanoid has recently been reported.
1 If the same type of ring cleavage may occur with a 6substituted bicyclo[3.l.O]hexane derivative, the reaction will provide a shorter route to prostanoid. In order to materialize this idea, it became necessary to know the stereochemistry of the intramolecular carbenoid addition and the ring-opening reaction of the resulting bicyclohexane.
๐ SIMILAR VOLUMES
In connection with our interest in the participation of bicyclobutonium type ions in solvolytic reactions, and more specifically in the solvolysis of bicyclo[2. 1. O]pentane-5-methanol derivatives, we have examined the reactions of the exe-and endo-bicyclo[3. l.O]hexane-6-methyl tosylates (I and II)