Chloramine derivatives

Witko-Sarsat, V., Nguyen Anh Thu, Knight, J., and Descamps-Latscha, B. (1992). Pholasin a new chemiluminescent probe for the detection of chloramines derived from human phagocytes. Free Radic. Biol. Med. 13 83-88. 

Reactive chloramine derivatives are produced in the first reaction step as a result of chlorination of the nitrogen by the /erf-butyl hypochlorite in the presence of potassium... 

The action of chlorine gas produces, for example, chloramine derivatives from herbicides, amino acids, peptides and proteins the active chlorine of these derivatives then... 

Peptides, for example, yield chloramine derivatives on exposure to chlorine gas these derivatives oxidize o-toluidine to a blue semiquinonoid dyestuff in the presence of acetic acid. 

The possibility of application of the quadrant rule for the IV-chloramine derivatives was discussed, and a similar rule was also proposed for the /V-cyano derivatives96. 

In addition to mcd, V-BrPO catalyzes the chlorination of phenol red to tetrachlorophenol blue [64], Chlorination of amines (e.g., taurine, ammonia, valine, serine, leucine) is also catalyzed by V-BrPO forming the stable chloramine derivative, even in the presence of dihydrogen peroxide. Unlike bromamines, the chloramine is not reduced by dihydrogen peroxide, or is reduced only very slowly [53],... 

The chloramine derivatives (ArS02NClNa) of a variety of other aryl-sulfonamides (Ar = phenyl, o-tolyl, p-chlorophenyl,/>-nitrophenyl, and o-carboalkoxyphenyl) have been used successfully in these catalytic oxy-aminations. Since only chloramine-T (Ar = p-tolyl) and chloramine-B (Ar = phenyl) are commercially available, we have developed a convenient procedure for generating the chloramines in situ for use in the modification involving phase-transfer catalysis. One simply stirs a suspension of the arylsulfonamide with an equivalent of sodium hypochlorite (Clorox) until a homogeneous solution is obtained. When this solution is used in the PTC method (see Ref. 2 for experimental details), the yields of oxyaminated product are comparable with those obtained with isolated chloramine salts. 

The chemistry of chloramines has been reviewed by Kovacic et al. (1970). In water, depending on pH and concentration, monochloramine (NH2CI), dichloramine (NHCI2), or trichloramine (NCI3), may be present, in addition to organic chloramines derived from amines. 

Most often, these determinations rely on the oxidation of an organic compound, usually a dye, by hydrogen peroxide or an oxoanion such as bromate, iodate, or peroxidisulfate or even a chloramine derivative. 

It was subsequently found by Sharpless and co-workers that the chloramine derived (eq 4) from terf-butylsulfonamide is an effective reagent for the osmium-catalyzed aminohydroxylation of a,/3-unsaturated amides (eq 5). In conjunction with a phase transfer catalyst, this chloramine also enables aziridination of alkenes... 

The disinfecting capability of hypochlorite is strongly inhibited by proteins and soils, as it is highly reactive and very quickly forms chloramine derivatives with nitrogen-containing compoimds. Therefore, it is important to use it only for disinfection of clean surfaces. For this reason, it is not an effective skin antiseptic, although it has the advantage of low skin toxicity. 

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