Alpha-Alkylidenecyclopentanones by Alpha-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate

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Alpha_Alkylidenecyclopentanones_by_.pdf
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1994
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Arnecke, Ralf
Köhler, Thomas
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Liebigs Annalen der Chemie. 1994, 1994(9), pp. 891-894. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199419940908
Zusammenfassung

An α-alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79% via a zinc chloride-catalyzed thioalkylation of the zinc enolate of methyl 2-oxocyclopentanecarboxylate (3) and subsequent saponification/desulfurization of the β-(phenylthio) ketone intermediates 5. For the saponificatioddesuiurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides.

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Fachgebiet (DDC)
540 Chemie
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Zinc enolates, thioalkylation of / Cyclopentanones, Alpha-alkylidene
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ISO 690ARNECKE, Ralf, Ulrich GROTH, Thomas KÖHLER, 1994. Alpha-Alkylidenecyclopentanones by Alpha-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate. In: Liebigs Annalen der Chemie. 1994, 1994(9), pp. 891-894. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199419940908
BibTex
@article{Arnecke1994Alpha-10040,
  year={1994},
  doi={10.1002/jlac.199419940908},
  title={Alpha-Alkylidenecyclopentanones by Alpha-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate},
  number={9},
  volume={1994},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={891--894},
  author={Arnecke, Ralf and Groth, Ulrich and Köhler, Thomas}
}
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