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Synthesis of cyclopentadienyl enaminonitriles from α-chlorovinyl p-tolyl sulfoxides and acetonitrile with three consecutive carboncarbon bond-formations

✍ Scribed by Tsuyoshi Satoh; Hiroyuki Ota

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
174 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of a-chiorovinyl p-tolyl sulfoxides with 5-equivalents of lithium carbanion of acetonitrile at -78 °C to room temperature afforded cyclopentadienyl enaminonitriles in high yields with three consecutive carboncarbon bond-formations. The mechanism of this reaction and some reactions of the enaminonitriles are reported.

📜 SIMILAR VOLUMES

Reaction of 1-Chlorovinyl p-Tolyl Sulfox
Reaction of 1-Chlorovinyl p-Tolyl Sulfoxides with Carbanion of Acetonitrile: A Novel Synthesis of Cyclopentanone Derivatives with Three Consecutive Carbon–Carbon Bond-Formations via the Enaminonitriles
✍ Tsuyoshi Satoh; Hiroyuki Ota 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 170 KB

AbstractÐTreatment of 1-chlorovinyl p-tolyl sulfoxides derived from ketones with cyanomethyllithium gave cyclopentadienyl enaminonitriles in high yields with three consecutive carbon±carbon bond-formations. However, the 1-chlorovinyl p-tolyl sulfoxides derived from aldehydes did not give good result