1886-64-2

Upstream product

• 4922-47-8 1-(phenylthio)cyclohex-1-ene 
• 917-54-4 methyllithium 
• 3559-72-6 1,1-dichloro-2-phenylthioethene 
• 591-51-5 phenyllithium 
• 1886-63-1 2-Butylmercapto-2-phenylmercapto-3,3-dimethyl-butan 
• 64228-38-2 2-butylsulfanyl-3,3-dimethyl-but-1-ene 
• 108-98-5 thiophenol 
• 563-80-4 3-methyl-butan-2-one 
• 17414-02-7 1,2-dimethylprop-1-enyl phenyl sulfide 
• 37457-08-2 cyclohexane-1,1-diylbis(phenylsulfane) 
• 56354-48-4 2,2,2-trichloroethyl phenyl sulfide 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 1886-62-0 2,2-bis(phenylthio)-3,3-dimethyl-butane 

Relevant academic research and scientific papers

General Synthesis of Alkenyl Sulfides by Palladium-Catalyzed Thioetherification of Alkenyl Halides and Tosylates

The cross-coupling reaction of alkenyl bromides with thiols catalyzed by palladium complexes derived from inexpensive dppf ligand is reported. These reactions occur under low catalyst loading and in high yields and display wide scope, including the coupling of bulky thiols and trisubstituted bromoolefins, and functional group tolerance. In addition, the thioetherification of less reactive chloroalkenes and, for the first time, alkenyl tosylates was accomplished using a catalyst generated from CyPFtBu alkylbisphosphine ligand.

ENOL THIOETHERS AS ENOL SUBSTITUTES. AN ALKYLATION SEQUENCE.

Ionic bromination of enol phenyl thiolethers forms predominantly to exclusively 2-(phenylthio)-3-bromo-1-alkenes, an enolonium equivalent. The allylic bromide participates in displacements with stabilized and nonstabilized nucleophiles. The ability to hydrolyze the enol thioethers to their corresponding ketones equates this sequence to an equivalence of an enolonium ion. The versatility of the sulfur in selective introduction of allylic hydroxyl and amino groups as well as the ability to directly replace the sulfur substituent by hydrogen or alkyl imparts special significance to this approach. The sequence is highly regio-and chemoselective. Applications include the synthesis of lanceol and bisabolene and the introduction of steroid side chains.

SYNTHESES AND REACTIONS OF PHENYLTHIO AND PROPYLTHIOACETYLENIC COMPOUNDS

Reactions of 2,2-dichlorovinyl sulfides and their sulfoxide and sulfone derivatives with tert-butoxide and with organolithium compounds have provided entries to chloroethynyl sulides, tert-butoxyethynyl sulfides and their derivatives.Application of these reactions for the synthesis of several functional derivatives is also described.Keywords: 2,2-dichlorovinyl sulfide; chloroethynyl sulfide; tert-butoxyethynyl sulfide; ethynyl sulfide; cyclobutenone