872220-84-3

Upstream product

• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 872220-83-2 2-(4-methoxybenzylsulfinyl)-N-methylbenzamide 
• 2527-66-4 2-methyl-1,2-benzisothiazole-3(2H)-one 
• 1315275-16-1 (S)-2-(benzylsulfinyl)-N-methylbenzamide 
• 1315275-23-0 N-methyl-2-(4-methyl-1-phenylpentylsulfinyl)benzamide 
• 1531-80-2 2-(benzylthio)benzoic acid 
• 101093-83-8 2-(4-methoxy-benzylsulfanyl)-benzoic acid 
• 20054-45-9 N-methyl-2-sulfanylbenzamide 
• 147-93-3 Thiosalicylic acid 
• 1050884-48-4 2-(4-trifluoromethyl-benzylsulfanyl)-benzoic acid 

Downstream Products

• 872220-83-2 2-(4-methoxybenzylsulfinyl)-N-methylbenzamide 
• 2527-66-4 2-methyl-1,2-benzisothiazole-3(2H)-one 
• 1315275-27-4 C₁₇H₁₆ClF₃ 
• 1315275-29-6 C₁₉H₂₀F₃NO 
• 132777-02-7 4-phenyl-1-<4-(trifluoromethyl)phenyl>butan-1-ol 
• 1315275-32-1 C₂₀H₂₅NOS 
• 1315275-17-2 (R)-2-(benzylsulfinyl)-N-methylbenzamide 
• 1315275-16-1 (S)-2-(benzylsulfinyl)-N-methylbenzamide 
• 1315275-23-0 N-methyl-2-(4-methyl-1-phenylpentylsulfinyl)benzamide 

Relevant academic research and scientific papers

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent

N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.

Synthesis of 1-aryl-tetralins and 4-aryl-benzopyrans by sulfoxide-mediated benzylic carbocation cyclizations

An alkylation/cyclization sequence, with both steps mediated by the ortho-N-methylformamido-phenylsulfinyl function, provided two new C-C bonds and an efficient entry to 1-aryl-tetralins and 4-aryl-benzopyrans. Scope and limits of the process have been studied in detail.