✦ LIBER ✦
ChemInform Abstract: Realization of Complete Regiochemical Control During the Conversion of Squarate Esters into Complex Linear and Angular Polyquinanes. The Consequences of Incorporating a Leaving Group into One of the Alkenyllithium Reactants.
✍ Scribed by L. A. PAQUETTE; J. DOYON
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 34 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Realization of Complete Regiochemical Control During the Conversion of Squarate Esters into Complex Linear and Angular
Polyquinanes. The Consequences of Incorporating a Leaving Group into One of the Alkenyllithium Reactants.
-The regioselectivity of the reaction cascade initiated by the 2-fold addition of alkenyl anions to diisopropyl squarate (I) is controlled by the choice of the leaving groups in the alkenyl-Li reactants. Alkoxides are mainly eliminated in the exocyclic mode, while the bromide ion is selectively eliminated in the intracyclic mode. The formation of a linear or angular polyquinane depends upon the position of the corresponding leaving group located either on the cyclic or acyclic alkenyl-Li reactant. -(