209391-91-3

Upstream product

• 119-61-9 benzophenone 
• 24824-93-9 chloromethyl p-tolyl sulfoxide 

Downstream Products

• 209391-60-6 [2-chloro-2-(p-tolylsulfinyl)ethene-1,1-diyl]dibenzene 
• 501-65-5 diphenyl acetylene 
• 1726-14-3 1,1-diphenyl-1-butene 
• 4541-89-3 2-chloro-1,1-diphenylethene 
• 209391-96-8 Acetic acid 2-chloro-1,1-diphenyl-2-(toluene-4-sulfinyl)-ethyl ester 

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.

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.