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By R. J. Cremlyn

Sulfur chemistry is changing into more and more vital because the position of this point is explored in either organic and environmental fields. After the preliminary chapters have mentioned the synthesis, reactivity, and houses of the compounds mostly, all the subsequent 9 chapters takes a selected sulfur containing sensible crew and expands the dialogue on man made methods. the ultimate bankruptcy seems to be on the significant makes use of of organo-sulfur compounds and their effect on organic and environmental components.

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The salts can then be separated by fractional crystallisation and the free optically isomeric sulfoxides liberated by acid hydrolysis. However, a more convenient synthetic procedure for the preparation of chiral sulfoxides of high optical purity is Andersen's method (see p. 30). Sulfoxides possess a non-planar pyramidal configuration; consequently, chiral sulfoxides can exist as optical enantiomers (see Chapter 5, p. 63). This is illustrated by the structures (33a) and (33b) showing the optical isomers of ethyl methyl sulfoxide (Figure 2).

Scheme 5 The oxidation of thiols follows a completely different course as compared with the oxidation of alcohols, because the capacity of the sulfur atom to form hypervalent compounds allows it to become the site of oxidation. Thiols are readily oxidised to disulfides by mild oxidants such as atmospheric oxygen, halogens or iron(III) salts (Scheme 6). This type of reaction is unique to thiols and is not undergone by alcohols, it is a consequence of the lower bond strength of the S-H as compared with the O-H bond, so that thiols are oxidised at the weaker S-H bonds, whereas alcohols are preferentially oxidised at the weaker C-H bonds (Scheme 7).

Asymmetric sulfonium salts (36) have a tetrahedral configuration; therefore, like the analogous chiral saturated carbon compounds, they can be resolved into optical enantiomers (see Chapter 6, p. 81). They are, however, generally less optically stable than sulfoxides, but in sulfonium salts the unshared electron pair can hold its configuration at ordinary temperatures, unlike nitrogen in quaternary ammonium salts, enabling their resolution to be achieved. 6a,7 The chemistry of hypervalent sulfur started in 1873 with the discovery of the unstable compound sulfur tetrachloride (SCl4).

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