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Ligand exchange reaction of sulfoxides in organic synthesis: A new synthesis of α-chloroketones from carbonyl compounds with one-carbon homologation

✍ Scribed by Tsuyoshi Satoh; Yasuhiro Mizu; Taku Kawashima; Koji Yamakawa


Book ID
107857442
Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
421 KB
Volume
51
Category
Article
ISSN
0040-4020

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✍ Tsuyoshi Satoh; Hideaki Unno; Yasuhiro Mizu; Yasumasa Hayashi 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 624 KB

A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give a-chloro a-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the a