Preparation of Sulphonic Acids

Preparation of Sulphonic Acids.—The main topics under this heading in the recent literature are very much the same as for the past ten years or more, involving 

Kleijn, C. J. Elsevier, H. Westmijze, J. Meijer, and P. Vermeer, Tetrahedron Lett., 1979,3101. 

Kleijn, H. Westmijze, K. Kruithof, and P. Vermeer, Reel. Trav. Chim. Pays-Bas, 1979, 98, 27. 

In contradiction to other reports claiming a cycloaddition mechanism, a sulphinylamine gives an cf-amino-sulphonic acid R NHCHR S03H with aldehydes through successive hydrolysis and then condensation and bisulphite-addition reactions.  

Additional Bibliography Y. Muramoto, H. Asakura, and H. Suzuki, Nippon Kagaku Kaishi, 1979, 

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The oxidation of sulphones leads to either a sulphonic acid (or a sulphonic acid derivative) or to sulphate. Such reactions have rarely been used for the preparation of sulphonic acids since these are usually readily available by other well-established routes. However, polyhalogenated sulphones can be oxidized relatively easily to sulphonic acids and these reactions will be discussed here. 

Preparation of sulphonic acids, esters, amides and halides... 

This chapter concerns the preparation of sulphonic acids and their derivatives and considers reactions occurring via one of the following three different methodologies ... 

By far the most common method for the industrial preparation of sulphonic acids and their salts is by direct sulphonation. Consequently, there are many hundreds of patents covering the industrial applications of these reactions, especially with reference to aromatic sulphonic acids, and the reader is referred to the reviews of Knaggs, Nunfaum and Schultz2 and of Gilbert5 for key references to this patent literature. 

Sulphites and hydrogen sulphites may be used for the preparation of sulphonic acids however, it is important to note that there is potential biological hazard involved in this process. This danger is discussed briefly below. 

This section covers the preparation of sulphonic acids by the oxidation of three different types of sulphur-containing functionality. Thiols, disulphides and related functional group oxidations are covered in the first part. The oxidation of both thiols and disulphides to sulphonic acids is one of the classical methods for the preparation of aliphatic and aromatic sulphonic acids. 

The preparation of sulphonic acids by the oxidation of sulphinic acids and their derivatives has been studied, by many workers, for at least the last hundred years. Much... 

Preparation of sulphonamides by carbon-sulphur(VI) bond formation has been used rather rarely compared with the preparation of sulphonic acids and sulphonyl halides (as discussed in Sections II.A and V.A of this chapter). There have, however, been a few interesting reports of this type of synthetic procedure and these are discussed below. 

Preparation of sulphonic acids, esters, amides and halides equation 107438, where R" is derived from the olefin, with a chloro substituent. 

In contrast, the conversion of cellulose with camphor-10-sulphonic acid via in situ activation with CDI is not efficient to obtain a chiral sulphonic acid ester of cellulose. Only very small amount of sulphonic acid ester functions can be introduced in agreement with results of the chemistry of low molecular weight alcohols regarding a much lower efficiency of CDI for the preparation of sulphonic acid esters [38],... 

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