2437-33-4

Upstream product

• 139-02-6 sodium phenoxide 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 108-95-2 phenol 
• 622-46-8 carbamic acid phenyl ester 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 42823-94-9 phenyl 4-cyanobenzenesulfonate 
• 1286023-30-0 phenyl 4-trifluoromethylbenzenesulfonate 
• 92964-93-7 1-naphthalenesulfonic acid phenyl ester 
• 14752-66-0 sodium p-chlorobenzenesulphinate 

Downstream Products

• 6621-62-1 4-chloro-benzenesulfonic acid-(2,4-dichloro-phenyl ester) 
• 80-33-1 chlorofensone 
• 4750-61-2 N-(p-chlorobenzyl)aniline 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 108-95-2 phenol 
• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 349397-05-3 4-chloro-N-(4-methoxybenzyl)benzenesulfonamide 
• 758640-21-0 N-Benzylaniline 
• 10504-90-2 N-benzyl-4-chlorobenzenesulfonamide 
• 15818-64-1 N-(4-methylbenzyl)aniline 
• 10504-94-6 4-chloro-N-(4-methylbenzyl)benzenesulfonamide 
• 116013-81-1 phenyl 4-ethylbenzenesulfonate 

Relevant academic research and scientific papers

Practical Electro-Oxidative Sulfonylation of Phenols with Sodium Arenesulfinates Generating Arylsulfonate Esters

A practical and sustainable synthesis of arylsulfonate esters has been developed through electro-oxidation. This reaction employed the stable and readily available phenols and sodium arenesulfinates as the starting materials and took place under mild reaction conditions without additional oxidants. A wide range of arylsulfonate esters including those bearing functional groups were produced in good to excellent yields. This reaction could also be conducted at a gram scale without a decrease of reaction efficiency. Those results well demonstrated the potential synthetic value of this reaction in organic synthesis.

Quantum Dot-Catalyzed Photoreductive Removal of Sulfonyl-Based Protecting Groups

This Communication describes the use of CuInS2/ZnS quantum dots (QDs) as photocatalysts for the reductive deprotection of aryl sulfonyl-protected phenols. For a series of aryl sulfonates with electron-withdrawing substituents, the rate of deprotection for the corresponding phenyl aryl sulfonates increases with decreasing electrochemical potential for the two electron transfers within the catalytic cycle. The rate of deprotection for a substrate that contains a carboxylic acid, a known QD-binding group, is accelerated by more than a factor of ten from that expected from the electrochemical potential for the transformation, a result that suggests that formation of metastable electron donor–acceptor complexes provides a significant kinetic advantage. This deprotection method does not perturb the common NHBoc or toluenesulfonyl protecting groups and, as demonstrated with an estrone substrate, does not perturb proximate ketones, which are generally vulnerable to many chemical reduction methods used for this class of reactions.

A new preparative method of aryl sulfonate esters by using cyclic organobismuth reagents

A new method for the preparation of aryl sulfonate esters by using a cyclic pentavalent bismuth is described. Aryl sulfonate esters are formed in good to high yields by treating 10-arylphenothiabismine 5,5-dioxides, m-chloroperoxybenzoicacid (m-CPBA)and various sulfonic acids in dichloromethane.

Unprecedented observation of sulfonamides in the transesterification of N-unsubstituted carbamates with sulfonyl chlorides

Sulfonamides have been identified as by-products in the base-mediated transesterification of N-unsubstituted carbamates with sulfonyl chlorides to give the corresponding sulfonates. A proposed mechanism and the synthesis of hindered 2,6-disubstituted arylsulfonates via this method are also reported.

Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile

The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 deg C have been studied. The reactons proceed competitevely by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analysis of the Hammet and Broensted coefficients together with the cross-interaction constants ρXY, ρYZ, and ρXZ, stepwise mechanisms are proposed in which the S-O bond cleavage proceeds by rate-limiting formation of a trigonal-bipyramidal pentacoordinate (TBP-5C) intermediate, whereas the C-O bond scission takes place by rate-limiting expulsion of the sulfonate anion (YC6H4SO3-) from a Meisenheimer-type complex.

Reactivity of sterically hindered aromatic sulfonic acid derivatives: VIII. * General mathematical model for catalytic sulfonylation of phenol

A general mathematical model is proposed for interpretation and prediction of the reactivity of sterically hindered arenesulfonyl chlorides in the catalytic sulfonylation of phenol. Some specific features of transition states in the catalytic and noncatal

REACTIVITY OF STERICALLY HINDERED DERIVATIVES OF AROMATIC SULFONIC ACIDS. III. EFFECT OF THE STRUCTURE OF ARENESULFONYL CHLORIDES ON THE KINETICS OF CATALYTIC SULFONYLATION OF PHENOL

The kinetics of the catalytic sulfonylation of phenol by benzenesulfonyl chlorides XArSO2Cl in benzene in the presence o

CATALYTIC SULFONYLATION OF PHENOL BY STERICALLY HINDERED SULFONYL CHLORIDES

The sulfonylation of phenol by substituted arenesulfonyl chlorides XArSO2Cl in the presence of triethylamine in benzene was studied by potentiometric titration.A linear relation was obtained between the logaritmhs of the catalytic rate constants and the steric constants Eso of the substituents in the sulfonyl chloride.The contribution from the induction and steric effects of the substituents at position2 to the kinetics of the process was assessed.It was concluded that the steric effect plays a predominant role over the induction and resonance effects.

SULFONYLATION OF PHENOLS IN THE PRESENCE OF PYRIDINE BASES

The sulfonylation of phenols by aromatic sulfonyl chlorides in the presence of pyridine bases in nitrobenzene was studied by potentiometric titration.A linear dependence was found between the logarithms of the catalytic constants and the ?-Hammett constan

STUDIEN ZUM VORGANG DER WASSERSTOFFUEBERTRAGUNG.61. Chemische Reaktivitaet und Halbstufenpotential Vergleichende Versuche am Beispiel einiger Arylsulfonsaeurederivate

In arylsulfonyl halides, the half-wave potentials of the corresponding chlorides and fluorides differ by more than 1000 mV, the fluoride being more negative; the influence of para-substituents is small for the chlorides, large for the fluorides.In agreement with the half-wave potentials, arylsulfonyl chlorides are considerably more reactive chemically than the corresponding fluorides.The O-selectivity found for P(O)F compounds is not observed in arylsulfonyl fluorides.Studies of competitive ester formation using primary and secondary alcohols and various arylsulfonyl chlorides yielded no clear analogy to the half-wave potentials.The primary alcohol is always sulfonated in preference to the secondary alcohol, whether the hydroxy functions are present in different molecules or the same molecule.In the latter case, the secondary hydroxyl function is then attacked in a further step by a second, different, arylsulfonyl chloride, giving the compounds 4-8.The further electroreduction of these diesters may be carried out in high yields, giving selective fission of one ester linkage only (that with the more positive potential) provided the difference in the half-wave potentials of the different ester linkages is sufficiently large.In the electroreductive fission the monosulfinic acid and the corresponding alcohol are liberated (see table II).In the competition reaction between phenol and 1:1 mixtures of tosyl chloride (A) and p-carboxyethyl-benzenesulfonyl chloride (B), the chloride with the more positive potential (B), E1/2=72 mV reacts quicker by a factor of 2.5.In competitive Finkelstein reactions, the selectivity was 1:11 at a difference in half-wave potentials of 760 mV (table IV).Arylsulfonates with free secondary alcohol functions may be oxidized smoothly and in high yield to the corresponding ketone using Na2Cr2O7 (3), without effecting the sulfonate linkage.The alkali hydrolysis of n-hexyl para-substituted arylsulfonates follows the Hammett relation but shows a lesser selectivity than was observed in the electroreductive fission of the same esters at the required potentials.Tables VI, VII and VIII concentrate on the preparative importance of the potential-controlled electroreductive fission of aliphatic and aromatic arylsulfonates.The corresponding hydroxy compounds are liberated in yields of up to over 90percent: N-alkyl- and N-aryl arylsulfonamides give analogous results. (table IX)