6213-85-0Relevant academic research and scientific papers
A simple method for the synthesis of sulfonic esters
Bhatthula, Bharath Kumar Goud,Kanchani, Janardhan Reddy,Arava, Veera Reddy,Marata Chenna Subbarao, Subha
supporting information, p. 1 - 16 (2020/07/27)
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.
The Hammett equation applied to the nucleophilic displacement of ions and ion pairs on substituted benzenesulphonates
Alunni, Sergio,Pica, Monica,Reichenbach, Gustavo
, p. 265 - 270 (2007/10/03)
Nucleophilic substitution on meta- and para-substituted methyl benzenesulphonates was studied with two chloride salts with different structures: NBu4Cl or KCl-Kryptofix 2,2,2. Treating the results with the Acree equation shows that the reaction proceeds by two reaction paths, one involving the chloride ion and the other, slower one, involving the ion pairs. Treating the results with the Hammett equation gives consistent data, and shows that ρ is positive and nearly the same for the two reaction paths (ρ ≈ +2). The reactivity of methyl p-nitrobenzenesulphonate was compared with that of the corresponding ethyl derivative, and it is shown that the methyl derivative reacts faster than the ethyl derivative in both paths. The results are interpreted based on the assumption that in both paths a negative charge is developed on the leaving group in the transition state, and that the activated complex is linear. Copyright
The Hammett equation and micellar effects on SN2 reactions of methyl benzenesulfonates - The role of micellar polarity
Brinchi, Lucia,Di Profio, Pietro,Germani, Raimondo,Savelli, Gianfranco,Spreti, Nicoletta,Bunton, Clifford A.
, p. 3849 - 3854 (2007/10/03)
Substituent effects on the reaction of H2O, OH-, and Br- with p-substituted methyl benzenesulfonates in cationic micelles of cetyl trialkylammonium ion surfactants (n-C16H33NR3X, X = OH, Br, R = Me, Et, nPr, nBu) and in water were analyzed by using the Hammett equation. Values of p in the various media confirm that micellar interfacial regions are less polar than water and polarities decrease with increasing bulk of the surfactant head-group. Wiley-VCH Verlag GmbH, 2000.
Methyl-Transfer Reactions. 6. Arenesulfonates as Nucleophiles and Leaving Groups. Methyl Trinitrobenzenesulfonate
Lewis, Edward S.,Smith, Michael J.,Christie, J. Joseph
, p. 2527 - 2531 (2007/10/02)
The methyl-transfer reactions from several substituted methyl arenesulfonates to potassium benzenesulfonate in sulfolane have been studied with respect to both rates and equilibria.Because the reactions were followed by proton NMR of the methoxy group, only cases of methyl arenesulfonates with quite distinct methoxy chemical shifts from the unsubstituted ester could be studied, and this, in fact, required the use of ortho substituents.Hammett plots for these data were thus impossible, but a plot of log k+ vs. log K, although somewhat scattered, did allow an estimation of the rate of the identity reaction for the unsubstituted compound.These methyl arenesulfonates, as well as methyl iodide, were placed roughly on the scale of equilibrium methylating agents studied earlier in the same solvent.Methyl 2,4,6-trinitrobenzenesulfonate is a very reactive substance not compatible with sulfolane.It is soluble and stable only in thionyl chloride among a large number of solvents attempted and methylates a few weak nucleophiles more extensively than methyl trifluoromethanesulfonate.
Perchlorate Esters. Part 3. Correlation of the Rates of Reaction of Arenesulphonate Ions with Methyl Perchlorate in Acetonitrile
Kevill, Dennis N.,Lin, Gloria Meichia L.,Bahari, Mohd S.
, p. 49 - 52 (2007/10/02)
Second-order rate coefficients for the reactions of acetonitrile solutions of tetra-n-butylammonium benzensulphonate and seven meta- and para-substituted derivatives with methyl perchlorate, at 0.3 deg C lead to a Hammet ρ value (-1.10 +/- 0.04) essentially identical to those previously reported for reactions with other powerful methylating agents.When silver ion is substituted for tetra-n-butylammonium ion, the second-oreder rate coefficients become concetration dependent and the fall of with increasing salt concetration can be rationalised on the basis of only free anions being reactive.The calculated degrees of dissociation are applied tothe previously studied silver0ion assisted reaction of silver toluene-p-sulphonate with methyl iodide.
CORRELATION OF THE RATES OF REACTION OF ARENESULFONATE IONS WITH THE TRIMETHYLOXONIUM ION IN ACETONITRILE
Kevill, Dennis N.,Lin, Gloria Meichia L.,Wang, An
, p. 715 - 717 (2007/10/02)
The kinetics of the reactions between trimethyloxonium hexafluorophosphate and a series of tetra-n-butylammonium arenesulfonates have been studied in acetonitrile at -23.4 deg C.With the oxonium salt concentration at about 0.01 M, two series of runs were carried out; Hammett plots of the second-order rate coefficients led to ρ values of -1.18 +/- 0.04 for 0.04 M arenesulfonate salt and -1.07 +/- 0.02 for 0.16 M arenesulfonate salt.Solvolysis kinetics for the trimethyloxonium ion in acetonitrile are also reported.
