Sulfide To sulfoxide

When the desired product is a sulfoxide sodium metaperiodate (NaI04) is an ideal reagent It oxidizes sulfides to sulfoxides m high yield but shows no tendency to oxidize sulfoxides to sulfones... 

Peroxy acids usually in dichloromethane as the solvent are also reliable reagents for converting sulfides to sulfoxides... 

Section 16 16 Oxidation of sulfides yields sulfoxides then sulfones Sodium metaper lodate IS specific for the oxidation of sulfides to sulfoxides and no fur ther Hydrogen peroxide or peroxy acids can yield sulfoxides (1 mole of oxidant per mole of sulfide) or sulfone (2 moles of oxidant per mole of sulfide)... 

In general, peroxomonosulfates have fewer uses in organic chemistry than peroxodisulfates. However, the triple salt is used for oxidizing ketones (qv) to dioxiranes (7) (71,72), which in turn are useful oxidants in organic chemistry. Acetone in water is oxidized by triple salt to dimethyldioxirane, which in turn oxidizes alkenes to epoxides, polycycHc aromatic hydrocarbons to oxides and diones, amines to nitro compounds, sulfides to sulfoxides, phosphines to phosphine oxides, and alkanes to alcohols or carbonyl compounds. 

Biomine in a two-phase system, H2O—CH2CI2, with KHCO can convert sulfides to sulfoxides in good yields (40). 

One equivalent of a peroxy acid or of hydrogen peroxide converts sulfides to sulfoxides two equivalents gives the conesponding sulfone. 

A number of studies describing the oxidation of sulfides to sulfoxides by biological oxidizing agents have been published over the years2 9,13,107- Microbial systems are often... 

Purified mammalian- and bacterial-derived enzymes were used by Oae, Walsh and their coworkers to oxidize sulfides to sulfoxides. The emphasis in these studies was on the characteristics of the enzymes rather than on the use of the enzymes to prepare homochiral sulfoxides. 

Oxidation of sulfides to sulfoxides and oxidation of thiols to disulfides... 

The oxidation of sulfides to sulfoxides are occasionally found to be unsatisfactory, since the resulting sulfoxides are easily oxidized to sulfones. In order to avoid the further oxidation of sulfoxides into sulfones, several oxidizing agents have been selected. Recently, we found that BTMA Bt3 is the most effective and satisfactory oxidizing agent for this purpose. That is, the reaction of sulfides with a calculated amount of BTMA Br3 and aq. sodium hydroxide in dichloromethane at room temperature, or in 1,2-dichloroethane under reflux, gave sulfoxides in good yields (Fig. 28) (ref. 36). 

Encapsulation in Y zeohte was also the method chosen to immobihze Mn complexes of C2-symmetric tetradentate hgands (Fig. 24) [75]. These materials were used as catalysts for the enantioselective oxidation of sulfides to sulfoxides with NaOCl. The lack of activity when the larger io-dosylbenzene was used as an oxidant was interpreted as an indication that the reaction took place inside the zeolite microporous system. Both the chemo- and enantioselectivity were dependent on the structure of the sulfide. (2-Ethylbutyl)phenylsulfide led to better results than methylphenylsulfide, although in all cases the enantioselectivity was low (up to 21% ee). 

This enantiomeric specificity has been of interest in other contexts, and stereospecific biotransformation has been observed. Examples include the enantiomeric oxidation of sulfides to sulfoxides (Chapter 11, Part 2) and steroid and triterpene hydroxylation (Chapter 7, Part 2). 

There has been considerable interest in the enantiomeric oxidation of sulfides to sulfoxides and illustrative examples include the following ... 

Sodium chlorite reacts very violently with organic compounds of divalent sulfur, or with free sulfur (which may ignite), even in presence of water. Contact of the chlorite with rubber vulcanised with sulfur or a divalent sulfur compound should therefore be avoided [1]. Application of factorial design techniques to experimental planning gave specific conditions for the safe oxidation of organic sulfides to sulfoxides using sodium chlorite or calcium hypochlorite [2],... 

Oxidation of Sulfides to Sulfoxides and Sulfones - Sodium Periodate-Silica... 

Rj = PhCH2 R2 = Ph Rj = Ph, n-C12ttz R2 = Me Scheme 6.34 Oxidation of sulfides to sulfoxides and sulfones by silica-supported sodium periodate. 

Oxidation of Sulfides to Sulfoxides - lodobenzene Diacetate-Alumina... 

Scheme 6.35 Oxidation of sulfides to sulfoxides by alumina-supported iodobenzene diacetate.

Nitrogen dioxide (NO ) reacts with a wide variety of functional groups and it is the reagent of choice for a number of synthetic transformations. For example, the selective oxidation of sulfide to sulfoxide by NO forms the basis for the commercial production of dimethyl sulfoxide (from dimethyl sulfide) via a catalytic procedure (see below).250 Some representative examples of oxidative transformations carried out with NO are presented in Chart 8. 

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