224319-37-3

Upstream product

• 289680-83-7 1-chloro-4-phenyl-1-(p-tolylsulfinyl)-2-butanol 
• 104-53-0 3-phenyl-propionaldehyde 
• 24824-93-9 chloromethyl p-tolyl sulfoxide 

Downstream Products

• 596119-12-9 tert-butyl 3-[chloro-(p-tolylsulfinyl)methyl]-5-phenylpentanoate 
• 1303964-06-8 (Z)-2-(2-phenylethyl)-4-phenyl-1-(p-tolylsulfinyl)but-1-en-3-yne 
• 1399809-98-3 4-chloro-2,2-dimethyl-3-(2-phenylethyl)cyclobutanone 
• 596119-48-1 4-(2-phenylethyl)-5-(p-tolylsulfanyl)-4,5-dihydro-3H-furan-2-one 
• 111748-85-7 4-(2-phenylethyl)-4,5-dihydro-3H-furan-2-one 

Relevant 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

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

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.