224319-53-3Relevant academic research and scientific papers
Synthesis of cyclopentadienyl enaminonitriles from α-chlorovinyl p- tolyl sulfoxides and acetonitrile with three consecutive carbon-carbon bond- formations
Satoh, Tsuyoshi,Ota, Hiroyuki
, p. 2977 - 2980 (1999)
Treatment of α-chlorovinyl p-tolyl sulfoxides with 5-equivalents of lithium carbanion of acetonitrile at -78 2°C to room temperature afforded cyclopentadienyl enaminonitriles in high yields with three consecutive carbon-carbon bond-formations. The mechani
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
Satoh, Tsuyoshi,Ota, Hiroyuki
, p. 5113 - 5122 (2007/10/03)
Treatment 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 α-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. (C) 2000 Elsevier Science Ltd.
