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Thioalkylation of Enolates, IV. α-Alkylidenecyclopentanones by α-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate

✍ Scribed by Arnecke, Ralf ;Groth, Ulrich ;Köhler, Thomas

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 490 KB
Volume: 1994
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199419940908

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✦ Synopsis

Abstract

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 saponification/desulfurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides.

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