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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

✍ Scribed by Tsuyoshi Satoh; Hiroyuki Ota

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
170 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 results. The mechanism of this reaction and the reaction of the enaminonitriles to convert cyclopentanone derivatives were investigated. Several a-carbanion of nitriles other than acetonitrile added to the 1-chlorovinyl p-tolyl sulfoxides at low temperature in good yield; however, they did not cyclize upon warming to room temperature.

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Synthesis of cyclopentadienyl enaminonitriles from α-chlorovinyl p-tolyl sulfoxides and acetonitrile with three consecutive carboncarbon bond-formations
✍ Tsuyoshi Satoh; Hiroyuki Ota 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 174 KB

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 e