40890-29-7

Upstream product

• 31536-21-7 isopropyl 4-methylbenzenesulfinate 
• 104310-56-7 1-methyl-4-(prop-1-yn-1-ylsulfinyl)benzene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 10486-08-5 sodium p-thiocresolate 
• 85143-15-3 C₁₁H₁₅N₃OS 
• 85143-00-6 4-Methyl-5-p-tolylsulfanyl-[1,2,3]selenadiazole 
• 33597-89-6 4-methylphenyl prop-2'-ynyl sulfide 

Downstream Products

• 75-05-8 acetonitrile 
• 14027-53-3 1-methyl-4-(prop-1-ynylsulfonyl)benzene 

Relevant academic research and scientific papers

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

Alkynylthioimidazolium Salts: Efficient Reagents for the Synthesis of Alkynyl Sulfides by Electrophilic Thioalkynylation

The efficient synthesis of a series of alkynylthioimidazolium salts through reaction of organozinc compounds with dibromo(imidazolium)sulfuranes is reported. Addition of Grignard reagents to these new species provided a highly modular, clean, and scalable access to a broad variety of alkynyl sulfides in good-to-excellent yields. The utility of this protocol was showcased by the preparation of alkynyl sulfides, which are particularly difficult to obtain or simply unavailable through the existing methodologies. In addition, the synthetic method was extended to the preparation of alkynyl selenides.

Selenium Heterocycles. XXXV. Synthesis and Pyrolysis of Aryloxy-, Arylthio-, and Arylseleno-1,2,3-selenadiazoles

A series of 4-substituted-5-arylthio-1,2,3-selenadiazoles, 4-substituted-5-arylseleno-1,2,3-selenadiazoles and 4-aryloxymethyl-1,2,3-selenadiazoles were synthesized.Pyrolysis of these compounds afforded the corresponding acetylenes XI, XIII (X = S, Se) and XII, respectively.Oxidation of 4-substituted-5-arylthio-1,2,3-selenadiazoles (XIV) with m-chloroperbenzoic acid gave 4-substituted-5-arylsulfinyl-1,2,3-selenadiazoles (XV) and 4-substituted-5-arylsulfonyl-1,2,3-selenadiazoles (XVI).