An Introduction to Organosulfur Chemistry by R. J. Cremlyn

By R. J. Cremlyn

Sulfur chemistry is changing into more and more very important because the position of this aspect is explored in either organic and environmental fields. After the preliminary chapters have mentioned the synthesis, reactivity, and homes of the compounds commonly, all the subsequent 9 chapters takes a selected sulfur containing practical team and expands the dialogue on man made techniques. the ultimate bankruptcy seems to be on the significant makes use of of organo-sulfur compounds and their influence on organic and environmental components.

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3 Structure-Chemical Relationship in Organosulfur Compounds 37 In hypervalent sulfur compounds like (37) and (38), the apical bonds formed by the p-orbitals are longer and more polar than the equatorial bonds. The special stability of many polycoordinated sulfur compounds is still concluded to be associated with the added orbital interaction with the energetically accessible 3d-orbitals. The discovery of sulfuranes has provided valuable insight into many nucleophilic substitution reactions on polycoordinate sulfur atoms and into ligand-coupling reactions which occur via σ-sulfurane intermediates.

E. 1. 8. L. Pauling, The Nature of the Chemical Bond, 1st Edn, Comell University Press, Ithaca, NY, 1939. 4 Thiols, Sulfides and Sulfenic acids 41 4 — Thiols, Sulfides and Sulfenic Acids Thiols, or thioalcohols (RSH),1,2a are sulfur analogues of alcohols and phenols in which the oxygen atom has been replaced by sulfur; they are derivatives of hydrogen sulfide in the same way that alcohols may be regarded as being derived from water. The volatile thiols have very unpleasant smells rather like the smell of hydrogen sulfide.

Scheme 30 In addition, sulfur monochloride (37) will react with p-chloroarylamines, like (45) in the presence of sodium hydroxide to give the sodium thiophenolate (46); this is the Herz reaction (Scheme 31) used in the synthesis of o-aminothiophenols, which are useful in the manufacture of thioindigo dyes (see Chapter 11, p. 221). 2 Synthesis of Organosulfur Compounds 27 Scheme 31 Thionyl chloride (39) in the presence of a few drops of DMF (catalyst) is a valuable reagent for the conversion of sulfonic acids (31) into the sulfonyl chlorides (32) (Scheme 32).

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