823213-45-2

Upstream product

• 24824-93-9 chloromethyl p-tolyl sulfoxide 
• 100-52-7 benzaldehyde 
• 161957-21-7 [(α-chloro)(p-tolylthio)methyl]diphenylphosphine oxide 
• 31238-58-1 [(p-tolylthio)methyl]diphenylphosphine oxide 
• 34125-84-3 chloromethyl p-tolyl sulfide 
• 161957-23-9 [(α-chloro)(p-tolylsulfinyl)methyl]diphenylphosphine oxide 

Downstream Products

• 1008-73-7 4-phenyldihydrofuran-2(3H)-one 
• 823213-97-4 4-phenyl-5-(p-tolylsulfanyl)dihydrofuran-2-one 
• 823213-64-5 4-chloro-N,N-dimethyl-3-phenyl-4-(p-tolylsulfinyl)butanamide 

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.

Multisubstituted α,β-unsaturated γ-lactones from 1-chlorovinyl p-tolyl sulfoxides and tert-butyl carboxylates using Pummerer-type cyclization as the key reaction

The addition reaction of 1-chlorovinyl p-tolyl sulfoxides, derived from aldehydes and chloromethyl p-tolyl sulfoxide, with the lithium enolate of tert-butyl carboxylates gave adducts in quantitative yields. Treatment of the adducts with trifluoroacetic anhydride in the presence of sodium iodide resulted in the formation of γ-lactones bearing a p-tolylsulfanyl group at the γ-position through Pummerer-type cyclization. Oxidation of the sulfanyl group to the sulfinyl group followed by thermal syn-elimination gave α,β-unsaturated γ-lactones (γ-butenolides) in moderate to good yields. Trapping the intermediates of the addition reaction with iodoalkanes gave alkylated adducts, from which α,γ;- and β,γ-disubstituted γ-butenolides were obtained. These procedures provide a good way to synthesize multisubstituted γ-butenolides from aldehydes. Georg Thieme Verlag Stuttgart New York.

A Horner-Wittig synthesis of 1-chlorovinyl sulfoxides

1-Chlorovinyl sulfoxides 1 were prepared by Horner-Wittig reaction of the readily accessible [(α-chloro)sulfinylmethyl)diphenylphosphine oxides 2 with aldehydes. Excellent Z-selectivity was observed in most cases.