Stereochemical issues on the fragmentation of non-enolisable β-heterosubstituted-cyclopentanones with wet and anhydrous potassium hydroxide |
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Authors: | Alain Krief Adrian Kremer |
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Institution: | Department of Chemistry, Facultés Universitaires N.-D. de la Paix, 61 Rue de Bruxelles, Namur B-5000, Belgium |
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Abstract: | Tandem Haller-Bauer-scission/Grob-fragmentation reaction of cyclopentanone bearing a leaving group in β-position involves antiperiplanar arrangements which can be also achieved from epimeric derivatives, probably due to the high flexibility of the five-membered ring. We have observed that epimeric compounds react at different rates if the leaving group is a halogen and leads to very different types of compounds when it is a mesyl group. |
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Keywords: | Fragmentation Hydroxide ion Wet potassium hydroxide Anhydrous potassium hydroxide Vinyl cyclopropane carboxylic acid |
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