Sulphonic acid ester

S. Patai and Z. Rappoport, eds.. The Chemistry of Sulphonic Acids, Esters and Their Derivatives, John Wiley Sons, Ltd., Chichester, U.K., 1991. 

Perfluoroalkanesulfomc Acids and Their Derivatives (Russ ) Huang, W, Chen Q Chern Sulphonic Acids, Esters, Their Derivatives 903-946 157... 

The kinetics of alkylation of aromatics with sulphonic acid esters have been... 

The chemistry of sulphonic acids, esters and their derivatives The chemistry of alkanes and cycloalkanes Supplement S The chemistry of sulphur-containing functional groups The chemistry of organic arsenic, antimony and bismuth compounds The chemistry of enamines (2 parts)... 

Metabolites formed during the decolourization of the azo dye Reactive red 22 by Pseudomonas luteola were separated and identified by HPLC-DAD and HPLC-MS. The chemical structures of Reactive red 22 (3-amino-4-methoxyphcnyl-/fhydroxyl-sulphonc sulphonic acid ester) and its decomposition products are shown in Fig. 3.92. RP-HPLC measurements were carried out in an ODS column using an isocratic elution of 50 per cent methanol, 0.4 per cent Na2HP04 and 49.6 per cent water. The flow rate was 0.5 ml/min, and intermediates were detected at 254 nm. The analytes of interest were collected and submitted to MS. RP-HPLC profiles of metabolites after various incubation periods are shown in Fig. 3.93. It was concluded from the chromatographic data that the decomposition process involves the breakdown of the azo bond resulting in two aromatic amines [154],... 

Fig. 3.93. The HPLC analysis on metabolites resulting from decolourization of reactive red 22 by Pseudomonas luteola (a) at the beginning of static incubation (IA = 3 639 667, /B = 130 140, Ic 116 243), (b) after static incubation for 4.7 h (/A = 2 231 542, /B = 230 559, Ic = 120 563), (c) after static incubation for 23.4 h (/A = 1 892 854, /B = 428 414, Ic = 205 169), (d) 3-amino t-methoxyphenyl /1-hydroxyl sulphone sulphonic acid ester (AMHSSAE), 90 per cent pure, 52 mg/1, and (e) products resulting from decolourization of Reactive red 22 by chemical reduction with SnCl2, (/A, /B, and 7C represent intensities of peaks A, B, and C, respectively). Reprinted with permission from J.-S. Chang et al. [154].

Further, by using Et3N.3HF in acetonitrile as solvent, they have demonstrated that electrolysis of benzyl nitriles, carboxylic acid esters, sulphonic acid esters and ketones give the corresponding monofluoro- or difluoro-compounds, depending on anode potential in yields of 30 - 70 %. 

Solid esters are easily crystallisable materials. It is important to note that esters of alcohols must be recrystallised either from non-hydroxylic solvents (e.g. toluene) or from the alcohol from which the ester is derived. Thus methyl esters should be crystallised from methanol or methanol/toluene, but not from ethanol, n-butanol or other alcohols, in order to avoid alcohol exchange and contamination of the ester with a second ester. Useful solvents for crystallisation are the corresponding alcohols or aqueous alcohols, toluene, toluene/petroleum ether, and chloroform (ethanol-free)/toluene. Carboxylic acid esters derived from phenols are more difficult to hydrolyse and exchange, hence any alcoholic solvent can be used freely. Sulphonic acid esters of phenols are even more resistant to hydrolysis they can safely be crystallised not only from the above solvents but also from acetic acid, aqueous acetic acid or boiling n-butanol. 

Nitriles Some amides, Sulphonic acids, Esters. Anhydrides. hydrocarbons. hydrazo and other... 

Carbon-13 n.m.r. spectroscopy has been used to study benzylisoquinoline and tetrahydroisoquinoline alkaloids and their JV-methyl quaternary salts.30 N-Benzylpapaverinium bromide has been shown to undergo aerial oxidation in alkaline solution to 2-benzyl-6,7-dimethoxyisoquinolone and to give bases of general structure (10) with methylamine, benzylamine, and pyrrolidine.31 Chlorosulphonation of papaverinol affords the sulphonic acid ester (11), mild hydrolysis of which yields the acid (12), which with diazomethane is esterified and dehydrated to (13).32 N-Methyl-l,2-dihydropapaverine has been shown by kinetic studies and orbital-symmetry requirements to rearrange to the salt (14) by the route previously postulated.33... 

Liebman JF (1991) Thermochemistry of sulphonic acids and their derivatives. In Patai S, Rappoport Z (eds) The chemistry of the sulphonic acids, esters and their derivatives. Wiley, Chichester, p 283... 

W. M. Horspool, Chem. Sulphonic Acids, Esters Their Deriv., 1991, 501, Wiley, Chichester, UK. 

B-58. Mason. TJ. (ed.), Sonochemistry, Royal Society of Chemistry, Cambridge, 1990. B-59. Patai, S and Rappoport, Z. (eds). Chemistry of Sulphonic Acids, Esters and their Derivatives, Wiley, Chichester, 1991. 

The chemistry of sulphonic acids, esters and their derivatives... 

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