224319-29-3Relevant academic research and scientific papers
Efficient one-pot synthesis of 1-chlorovinyl p-tolyl sulfoxides from aldehydes and ketones by the Horner-Wadsworth-Emmons reaction
Kimura, Tsutomu,Kobayashi, Gen,Ijima, Shiori,Saito, Sae,Imafuji, Aki,Satoh, Tsuyoshi
, (2017/10/27)
A variety of 2-monosubstituted and 2,2-disubstituted 1-chlorovinyl p-tolyl sulfoxides was synthesized through a one-pot procedure by the Horner-Wadsworth-Emmons reaction of carbonyl compounds with [chloro(diethoxyphosphoryl)(p-tolylsulfinyl)methyl]lithium, which was generated from diethyl chlorophosphate, chloromethyl p-tolyl sulfoxide, and lithium diisopropylamide in advance. The in situ-prepared sulfoxides were directly converted into alkynes via the sulfoxide/magnesium exchange reaction with i-PrMgCl and the subsequent Fritsch-Buttenberg-Wiechell rearrangement of the resulting magnesium alkylidene carbenoids.
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.
