Preparation of Sulfoxide

Several methods have been widely used in the preparation of sulfoxide complexes, and these are outlined below. Routes specific to given systems are dealt with in Section V. 

Remarkably, there is a noticeable lack of general methods for the asymmetric preparation of chiral sulfoxides from sulfides. The most satisfactory method would be a generally applicable enantioselective sulfoxidation reaction which would allow the preparation of sulfoxides from any prochiral sulfide with high ee s and in which the sulfoxide would be amenable to enantioselective preparation in both senses. 

Aqueous hydrogen peroxide is the oxidant of choice for the preparation of sulfoxides.367 Acetic acid is often used as the solvent due to its specific solvation rather than due to peracetic acid formation.368 Alcohols and ketones have been... 

Organic hydroperoxides are generally used for the preparation of sulfoxides from sulfides, - while sulfones can be obtained in neutral organic solvents in the presence of metal catalysts such as V, Mo and Ti oxides at 50-70 C. Two polymer-supported reagents which involve peroxy acid groups and bound hypervalent vanadium(V) and molybdenum(VI) compounds have been developed for facile oxidation of sulfoxides to sulfones. 

Table 7 Preparation of sulfoxides 200 from dienes 199 and trisulfide 2-oxide 198...

In our preliminary report on the use of MMPP we showed that tetra-hydrothiophene could be oxidised selectively to afford either the sulfoxide or the sulfone [5], and using UHP at room temperature we were only able to isolate the sulfone [11]. Careful control of the amount of MMPP used has allowed the preparation of sulfoxides as shown in Eqs. (39 and 40) [47], while use of an excess of MMPP allows sulfones (Eqs. 41 and 42) to be isolated in good yields [48,49]. 

The preparation of sulfoxide (14) also utilises the readiness of the unsaturated side-chain of isosafrol to addition reactions. The sulfur atom ot the thiocther, formed by the reaction of isosafrol with octylmercaptane, is oxidised to a sulfoxide group (Synerholm, 1944, 1946 Syncrholm and Cullman, 1947 Synerholm and Hartzell, 1945). 

Preparation of sulfoxides can be achieved by use of various oxidants diphenyl,898 dibenzyl,596 bis-(4-acetylaminophenyl),596 and diethyl sulf-... 

The more important of the other oxidizing agents reported for the preparation of sulfoxides are peracids602,603 (in equivalent amounts), sodium metaperiodate,604 chromic acid in glacial acetic acid,605 and nitric acid.606... 

Hypervalent iodine reagents are commonly used for the oxidation of organosulfiir compounds. Applications of hypervalent iodine reagents for the preparation of sulfoxides, including enantioselective oxidations of organic sulfides, have been summarized in reviews [519,520]. 

Pees B., Sindt M., Paul J.M. Mieloszynski J.L. (2002). Synthese et caracteiisation physico-chimiques de polyaaylates d (0-p>erfluorooctyl-atkyle effet p ir- impair. Eur. Polym. Jour, vol.38, n°5, p>p. 921-931 (May 2002), ISSN 0014-3057 Pees B., Paul J.M., Oget N, Sindt M., Mieloszynski J.L. (2003). Synthesis of fluoro-substituted monomers bearing a functionalised lateral chain. Part 2 Preparation of sulfoxides and sulfones containing monomers, J. Fluor.Chem., voLl24, n°2, pp.l39-146 (December 2003) ISSN 0022-1139... 

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