Dimethyl sulfoxide chlorite

Sodium chlorite, 423 Sodium cyanide-Alumina, 423 Sodium Cyanide-Dimethyl sulfoxide, 423 Sodium cyanoboro hydride, 424-426 Sodium dicarbonylcyclopentadienyliron, 426... 

Alkoxy-3-chloro-3//-diazirines are obtained by the chlorination (aqueous sodium hypo-chlorite/dimethyl sulfoxide) of the corresponding amidines. They serve as precursors for the synthesis of 3-fluoro derivatives via the reaction with anhydrous tetrabutylammonium fluoride (for an improved procedure for the dehydration of commercial tetrabutylammonium fluoride trihydrate, see ref 26). This is a much simpler method than the earlier described preparation of 3-fluoro-3-methoxy-37/-diazirine involving the elemental fluorination reaction and a shatteringly explosive fluoronitrogen intermediate. 

A very useful oxidant for the conversion of aldehydes into carboxyhc acids is sodium chlorite [115]. However, since other oxidants such as hypochlorite and chlorine dioxide are formed in the course of this oxidation, the product yield can be diminished. In order to avoid this effect, scavengers such as hydrogen peroxide [116-118], dimethyl sulfoxide [116], sulfamic acid [116, 119-121], resorcinol [119] or 2-methylbu-tene [122-124] have been added. Chlorites are particularly appropriate for the oxidation of functionalized aliphatic [116-118, 122], a,P-unsaturated [116, 117, 120, 123] and aromatic aldehydes bearing electron-withdrawing groups [116,117, 121, 124]. In the case of donor substituents on the aromatic ring, chlorinated compounds are formed as byproducts [116]. 

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