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By R. J. Cremlyn

Sulfur chemistry is changing into more and more very important because the function 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 ordinarily, all the subsequent 9 chapters takes a selected sulfur containing sensible workforce and expands the dialogue on man made techniques. the ultimate bankruptcy seems on the significant makes use of of organo-sulfur compounds and their impression on organic and environmental parts.

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Extra resources for An Introduction to Organosulfur Chemistry

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Organic Sulfur Chemistry (Eds F. Bernardi, I. G. M. Csizmadia and A. Mangini), Elsevier, Amsterdam, 1985: (a) S. Oae, Chap. 1; (b) R. A. Hayes and J. C. Martin, Chap. 8, p. 408. 7. 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Acids Thiols, or thioalcohols (RSH),1,2a are sulfur analogues of alcohols and phenols in which the oxygen atom has been replaced by sulfur; they are derivatives of hydrogen sulfide in the same way that alcohols may be regarded as being derived from water.

For instance, in the reaction of methyl phenyl sulfide (21) and butyllithium, the resultant carbanion is stabilised by resonance structures which utilise the 3d-orbitals of sulfur (Scheme 5). g. in dimethyl sulfoxide (DMSO) (Scheme 6). 3 Structure-Chemical Relationship in Organosulfur Compounds 33 Scheme 6 Dimsylsodium (22) is an important reagent and it can be used for carbon-carbon bond formation (see Chapter 10, p. 187). DMSO may also be used in the Moffatt oxidation (see Chapter 5, p. 66) and by alkylation it can be converted into the corresponding dimethylsulfoxonium ylide which is valuable in organic synthesis (see Chapter 10, p.

Scheme 25 Sulfuric acid Concentrated or fuming sulfuric acid (oleum) is widely used for the direct sulfonation of aromatic compounds (see Chapter 7, p. 5,6 The active sulfonating agent in sulfuric acid is the electrophile sulfur trioxide, and the sulfonating power of sulfuric acid is proportional to the concentration of SO3. Consequently, fuming sulfuric acid, which contains excess sulfur trioxide, is a more powerful sulfonating agent than concentrated sulfuric acid. The sulfonation of an aromatic hydrocarbon is depicted in Scheme 26.

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