40976-97-4

Upstream product

• 79894-51-2 2,2,2-trichloroethyl phenyl sulfoxide 
• 56354-48-4 2,2,2-trichloroethyl phenyl sulfide 
• 931-59-9 benzenesulfenyl chloride 
• 3559-72-6 1,1-dichloro-2-phenylthioethene 

Downstream Products

• 74031-55-3 2-Benzenesulfinylethynyl-2-ethyl-malonic acid diethyl ester 
• 79894-55-6 tert-butoxyethynyl phenyl sulfoxide 
• 14090-83-6 methyl 2-phenylsulfinylacetate 
• 127492-03-9 1-(phenylsulfinyl)-2,2,2-triethoxyethane 
• 96204-67-0 C₂₀H₁₄N₂O₅S₃ 
• 107673-10-9 ((E)-2-Chloro-2-methoxy-ethenesulfonyl)-benzene 
• 93845-21-7 2-((E)-2-Benzenesulfonyl-1-methoxy-vinyl)-2-ethyl-malonic acid diethyl ester 
• 93845-22-8 2-(2-Benzenesulfonyl-acetyl)-2-ethyl-malonic acid diethyl ester 
• 93845-16-0 2-((Z)-2-Benzenesulfinyl-1-methoxy-vinyl)-2-ethyl-malonic acid diethyl ester 
• 93845-18-2 2-Ethyl-2-((Z)-1-methoxy-2-phenylsulfanyl-vinyl)-malonic acid diethyl ester 
• 93845-26-2 2-(2-Benzenesulfonyl-acetyl)-2-isopropyl-5-methyl-cyclohexanone 
• 93845-20-6 2-Ethyl-2-(2-phenylsulfanyl-acetyl)-malonic acid diethyl ester 
• 93845-27-3 8a-(2-Benzenesulfonyl-acetyl)-octahydro-naphthalen-1-one 
• 93845-25-1 2-(2-Benzenesulfonyl-acetyl)-2-methyl-cyclohexanone 

Relevant academic research and scientific papers

One-Flask, Regiospecific Conversions of Allylic Alcohols into Two-Carbon-Extended, Conjugated Dienoate Esters. Use of a New Sulfinyl Orthoester

Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100 deg C sequentially via a sigmatropic rearrangement and then a β-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45-95percent yields.This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific γ-attachment of a two-carbon (ethoxycarbonyl)methylene unit via the synthetic equivalent of an SN2' process.Two examples are given in which rationally designed dienoates 20 and 24, prepared via this one-flask process and carrying a pendant alkene unit, undergo intramolecular 2+4 cycloaddition producing bicyclic cyclohexenes 21 and 25.

NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XIV. REACTION OF β,β-DICHLOROVINYL PHENYL SULFOXIDE WITH SODIUM METHOXIDE AND THIOPHENOLATES

The kinetics of the nucleophilic substitution of chlorine atoms in β,β-dichlorovinyl phenyl sulfoxide by sodium methoxide and substituted thiophenolates in methanol were investigated.The substitution of the first chlorine atom in reaction with sodium methoxide is realized by an elimination-addition mechanism, while substitition of the second chlorine atom is realized by a direct substitution mechanism.In the reaction with sodium thiophenolates both chlorine atoms are substituted by a direct substitution mechanism.A comparison is made of the reactivities of β,β-dichlorvinyl phenyl sulfoxide and β,β-dichlorovinyl phenyl sulfone, and the effect of the activating group at the α position is discussed.

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