110210-21-4

Upstream product

• 110210-15-6 (E)-1-iodo-2-(4-methylphenylsulfonyl)-1-(4-methylphenyl)ethene 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 98-59-9 p-toluenesulfonyl chloride 
• 766-97-2 4-n-methylphenylacetylene 
• 1950-78-3 p-toluenesulfonyl iodide 

Downstream Products

• 86971-42-8 (E)-1-methyl-4-(4-methylstyrylsulfonyl)benzene 

Relevant academic research and scientific papers

Synthesis of vinyl sulfoxides using sulfinyl chlorides and olefins

A general method for synthesis of vinyl sulfoxides, using sulfinyl chlorides and olefins as starting materials and DBU as an HCl scavenger, has been developed. Vinyl sulfoxides were obtained from the ZnCl2 catalysed addition of sulfinyl chlorides to olefins followed by the elimination with DBU. However, the direct reaction of sulfinyl chlorides with olefins in the presence of DBU, usually leads to generation of vinyl sulfones. The sulfonyl radicals generated from the DBU-mediated disproportionation of the sulfinyl radicals undergo addition-elimination reaction with olefins to give vinyl sulfones.

Silver(I)-mediated reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides: Unexpected formation of vinyl sulfones

A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yields and with Z-selectivity. A free radical mechanism has been proposed to account for the formation of the products.

Addition of Arenesulphonyl Iodides to Substituted Phenylacetylenes

The products of the addition of toluene-p-sulphonyl iodide to substituted phenylacetylenes (and styrenes) are studied.The regiospecificity and stereoselectivity of trans addition to acetylenes is inferred from (1)H n.m.r. spectroscopy.The effect of substituents on the reactivity of substituted phenylacetylenes towards substituted beenzenesulphonyl radicals generated by photolysis of sulphonyl iodides is studied.Phenylacetylenes with electron-donating substituents react faster.Relative reactivities yield good Hammet-Brown correlations showing the electrophilic character of sulphonyl radicals towards phenylacetylenes.The selectivity of the addition (measured by ρ) of different sulphonyl radicals towards the same set of acetylenes ranges from -0.53 to -0.93 and shows a tendency to be smaller for benzenesulphonyl iodides carrying electron donating substituents.Results are discussed in terms of polar effects on the transition state and frontier molecular orbital theory.