209391-68-4

Upstream product

• 24824-93-9 chloromethyl p-tolyl sulfoxide 
• 98-86-2 acetophenone 

Downstream Products

• 673-32-5 1-Phenylprop-1-yne 
• 86474-76-2 (Z)-2-(2-phenylprop-1-en-1-yl)thiophene 
• 86474-75-1 (E)-2-(2-phenylprop-1-en-1-yl)thiophene 
• 1158178-85-8 C₁₃H₁₂O 
• 865368-69-0 C₁₃H₁₂O 
• 823213-94-1 4-methyl-4-phenyl-5-(p-tolylsulfanyl)dihydrofuran-2-one 
• 50598-37-3 4-methyl-4-phenyldihydrofuran-2(3H)-one 
• 86474-75-1 2-(β-methylstyryl)thiophene 
• 823213-58-7 4-chloro-3,N,N-trimethyl-3-phenyl-4-(p-tolylsulfinyl)butanamide 
• 16917-32-1 (E)-2-chloro-1-methyl-1-phenylethene 

Relevant academic research and scientific papers

Fritsch-Buttenberg-Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch-Buttenberg-Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using13C-labeled sulfoxides and by using DFT calculations.

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.

Magnesium alkylidene carbenoids: Generation from 1-halovinyl sulfoxides with Grignard reagents and studies on their property, mechanism, and some synthetic uses

Magnesium alkylidene carbenoids were generated from 1-halovinyl sulfoxides, derived from ketones and aryl halomethyl sulfoxide, through the ligand exchange reaction of sulfoxides with Grignard reagents. The generated magnesium alkylidene carbenoids were found to be stable at -78 °C for over 30 min. The carbenoids reacted with aldehydes to give the adducts in moderate yields; however, they were found to be relatively unreactive to usual electrophiles. The generated magnesium alkylidene carbenoid exists in equilibrium between an α-halo alkenyl Grignard reagent and an alkylidene carbene-magnesium halide complex. Halogen exchange and geometrical isomerization of the alkylidene carbenoids were observed. 1-Chlorovinyl sulfoxides reacted with excess aryl Grignard reagents to give alkenyl Grignard reagents having an aryl group. These Grignard reagents reacted with several electrophiles to give tetra-substituted olefins in moderate to good yields.