86602-23-5

Upstream product

• 536-74-3 phenylacetylene 
• 933-01-7 4-chloro-benzenesulfenyl chloride 
• 98-60-2 4-chlorobenzenesulfonyl chloride 

Downstream Products

• 532-27-4 1-chloroacetophenone 
• 344882-49-1 (E)-2-chloro-1-(4-chlorophenylsulphonyl)-1-phenylethene 
• 86602-25-7 (Z)-1-chloro-2-(4-chlorophenylthio)-1-phenylethene 
• 31599-09-4 (Z)-1-chloro-2-(4-chlorophenylsulphonyl)-1-phenylethene 
• 24422-79-5 α-methylbenzyl 4-chlorophenyl sulfone 
• 100716-73-2 4-chlorophenyl 2-phenylethyl sulphone 

Relevant academic research and scientific papers

Copper-Catalyzed Vicinal Chloro-thiolation of Alkynes with Sulfonyl Chlorides

A copper-catalyzed vicinal chloro-thiolation of alkynes with inexpensive and diversified sulfonyl chlorides RSO2Cl (R = aryl, alkyl) has been developed. This practical and scalable reaction could be used for the construction of a number of unexplored bioactive chlorothiolated alkenes. Internal alkynes could also undergo the chloro-thiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via copper-mediated homolysis of the S-Cl bond.

Addition of 4-Chlorobenzenesulphenyl Chloride to 3-Methylbut-1-yne, Hex-1-yne, and Phenylacetylene: Isomerisation and Hydrolysis of the Adducts

The addition of (4-ClC6H4SCl, (2), to RCH(*)CH, (1; R=Pri, Bun), gives (E)-4-ClC6H4(R)C(*)C(H)Cl, (E)-(3), and (E)-4-ClC6H4(H)C(*)C(R)Cl, (E)-(4) in a fixed ratio; the addition to (1; R=Ph) gives regiospecifically (E)-(3; R=Ph) in ethyl acetate, but different proportions of (E)-(3) and (E)-(4) (R=Ph), in chloroform, sym-tetrachloroethane, and acetic acid.With an excess of the sulphenyl chloride (2), (E)-(3) and (E)-(4) isomerize to (Z)-(4) (same R).The sulphuric-acid catalysed hydrolysis of (E)-(3; R=Pri, Bun, Ph) gives α-chloroketones RCOCH2Cl(5) (same R).The (E)-(4) isomers do not hydrolyse.