Aromatic sulphonation II: Orientation in the sulphonation of toluene

A variety of methods for the preparation of selectively mono-, di-or tri-labelled arenes are reviewed. The review concentrates on those for which the application to labelled synthesis has been demonstrated. Further methods, the application of which to labelled synthesis appears viable but which have not been reduced to practise, are included also. The available methods provide a range of substitution patterns.

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Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Gregson

Herbert

Row

2011

Labelled Comp Radiopharmac

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Aromatic sulphonation III: Sulphonation of benzenesulphonic acid and m‐toluenesulphonic acid in fuming sulphuric acid

Cerfontain¹

1961

Recl. Trav. Chim. Pays‐Bas

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The kinetics of the sulphonation of berizenesulphonic acid and m-toluenesulphonic acid have been measured in oleum, containing 0.7 to 43.6% of sulphur trioxide * at 25". The reaction is first order with respect to the sulphonic acid. The kinetics are shown to be consistent with the sulphonation mechanism proposed by Brand 1, in which the reaction proceeds by a stepwise attachment of SO3 and H+ to the substrate, followed by the loss of a proton from the benzene ring.Sulphonation of the protonated sulphonic acid cannot be ruled out. Its contribution to the total rate of sulphonation is regarded as small in view of its electrophilic nature.

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Aromatic sulphonation IV Kinetics and mechanism of the sulphonation of benzene in aqueous sulphuric acid

Kaandorp

Cerfontain

Sixma

1962

Recl. Trav. Chim. Pays‐Bas

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The kinetics of the sulphonation of benzene have been measured at 5.0", 25.0" and 45.0" in aqueous sulphuric acid solutions, varying from 77.6 to 99.2 wt-% HzS04. In addition, sulphonation rate measurements have been made at 5.0" in 98.8 wt-% HzS04 containing various concentrations of sodium bisulphate. All reactions were found to be first order with respect to benzene. The kinetics are discussed in terms of the mechanism:It is suggested that sulphur trioxide or, though less probable, the sulphuric acid solvate of sulphur trioxide S03(H2S04) or disulphuric acid (H&07), is the sulphonating entity X and that kl < k2 1 B / + k3. No kinetic distinction can be made between the deprotonation by reaction [2] and the less probable intramolecular proton shift (reaction [3]).A comparison between the mechanisms of sulphonation in aqueous and fuming sulphuric acid furnishes additional evidence that so3, instead of S03(HzS04) or HzSz07, should be regarded as the sulphonating entity.

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Aromatic sulphonation II: Orientation in the sulphonation of toluene

Cited by 19 publications

References 18 publications

Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Aromatic sulphonation III: Sulphonation of benzenesulphonic acid and m‐toluenesulphonic acid in fuming sulphuric acid

Aromatic sulphonation IV Kinetics and mechanism of the sulphonation of benzene in aqueous sulphuric acid

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