22017-57-8

Upstream product

• 64-17-5 ethanol 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 141-52-6 sodium ethanolate 
• 100-66-3 methoxybenzene 
• 696-63-9 4-Methoxybenzenethiol 
• 64-67-5 diethyl sulfate 
• 51-28-5 2,4-Dinitrophenol 
• 917-58-8 potassium ethoxide 
• 154853-46-0 2,4-dinitrophenyl 4-methoxybenzenesulfonate 

Relevant academic research and scientific papers

A simple method for the synthesis of sulfonic esters

An efficient and simple approach for the direct synthesis of aryl and heteroaryl sulfonic esters was developed using DMS and DES as alkoxysulfonylation reagents. The reaction is operationally simple and scalable. This protocol does not require solvent, expensive catalysts, base, ligand additives or other reagents. A wide range of sulfonic esters were synthesized in moderate to good chemical yields. This method has the advantage of low cost, facile and tolerated a wide range of substrates.

Electrochemical synthesis of sulfinic esters from alcohols and thiophenols

Electrochemical oxidative couplings between S[sbnd]H and O[sbnd]H bonds are achieved herein directly from readily-available alcohols and thiophenols, affording a series of diverse sulfinic esters. This strategy can take advantage of 6 equivalents of alcohol, relative to thiophenol, to achieve moderate to good yields, without the assistance of any metallic catalysts, bases, and additional oxidants.

Synthesis and reactivity of phosphine-arenesulfonate palladium(II) alkyl complexes that contain methoxy substituents

Phosphine-arenesulfonate ligands that contain 1-3 methoxy substituents on the benzo linker, P(2-OMe-Ph)2(2-SO3Na-5-OMe-Ph) (Na[1a]), P(2-MeO-Ph)2(2-SO3Na-4,5-(OMe)2-Ph) (Na[1b]) and P(2-MeO-Ph)2

Photoinduced Oxidative Cross-Coupling for O-S Bond Formation: A Facile Synthesis of Alkyl Benzenesulfonates

We have developed a photoinduced oxidative cross-coupling of thiophenols with alcohols for O-S bond formation. The protocol uses visible light, a metal-free photocatalyst, and oxygen as the oxidant for the selective synthesis of alkyl benzenesulfonates; no ligand co-additive is necessary. Mechanistic studies suggested that the disulfide and alkyl benzenesulfinate are involved as intermediates and that the transformation proceeds by a radical pathway.

A kinetic study on nucleophilic displacement reactions of aryl benzenesulfonates with potassium ethoxide: Role of K+ ion and reaction mechanism deduced from analyses of LFERs and activation parameters

Pseudofirst-order rate constants (kobsd) have been measured spectrophotometrically for the nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates 4a-f and Y-substituted phenyl benzenesulfonates 5a-k with EtOK in anhydrous ethanol. Dissection of k obsd into kEtO- and kEtOK (i.e., the second-order rate constants for the reactions with the dissociated EtO - and ion-paired EtOK, respectively) shows that the ion-paired EtOK is more reactive than the dissociated EtO-, indicating that K + ion catalyzes the reaction. The catalytic effect exerted by K + ion (e.g., the kEtOK/kEtO- ratio) decreases linearly as the substituent X in the benzenesulfonyl moiety changes from an electron-donating group (EDG) to an electron-withdrawing group (EWG), but it is independent of the electronic nature of the substituent Y in the leaving group. The reactions have been concluded to proceed through a concerted mechanism from analyses of the kinetic data through linear free energy relationships (e.g., the Bronsted-type, Hammett, and Yukawa-Tsuno plots). K+ ion catalyzes the reactions by increasing the electrophilicity of the reaction center through a cyclic transition state (TS) rather than by increasing the nucleofugality of the leaving group. Activation parameters (e.g., ΔH? and ΔS?) determined from the reactions performed at five different temperatures further support the proposed mechanism and TS structures.

Limitations of the Transition-state Variation Model. Part 3. Solvolyses of Electron-rich Benzenesulphonyl Chlorides

Rate constants for solvolyses of 4-methoxy-2,6-dimethylbenzenesulphonyl chloride 3 (Z = OMe) and of 4-methyl- and 4-methoxybenzenesulphonyl chlorides 4 (Z = Me and OMe) are reported for aqueous binary mixtures with acetone, ethanol and methanol.Some additional rate constants are reported for aqueous acetonitrile and dioxane mixtures, as well as product selectivities (S) in alcohol-water mixtures.For each binary mixture, rates of solvolyses of 3 (Z = OMe) vs.YCl or Y are approximately bilinear.As water is added to alcohol, S values for solvolyses of 3 (Z = OMe) pass through a maximum and for solvolyses of 4-methoxybenzenesulphonyl chloride 4 (Z = OMe) the position of the maximum shifts to more aqueous media.For solvolyses of 4-methyl-benzenesulphonyl chloride 4 (Z = Me), S values are shifted such that they reach a plateau rather than a maximum, and the rate-rate profiles with YCl are approximately linear rather than bilinear.All of rate-rate profiles show 'dispersion' into separate correlations for the various binary mixtures.These substituent effects follow the same trends as corresponding solvolyses of benzoyl chloride and strengthen recent proposals that solvolyses of 3 (Z = Me) proceed via competing (dual) reaction channels.