Chloramine-T trihydrate

The commercially available chloramine-T trihydrate (TsNNaCl 3H20) could also be used directly as the oxidant, although slightly more dilute concentrations (0.2 m vs. 0.5 m) had to be employed to ensure comparable yields. The applicability of this trihydrate version to large-scale syntheses was demonstrated by the aziridination of cyclopentene on a 0,5 mol scale reaction, providing 6-tosylazabicyclo-[3.1.0]hexane in 80% isolated yield (Scheme 12.14). 

In general, nitrilimines are generated in the presence of a suitable dipo-larophile. Thus, heating an equimolar mixture of hydrazone 313, alkene 314, and chloramine-T trihydrate in ethanol under reflux for 3 h provided pyrazolines 315 in 68-90% yield [81]. The cycloaddition in all the cases was regiospecific as indicated by NMR (Table 23). 

Olefins by reaction of alkyl phenyl tellurides with chloramine-T (typical procedure). A solution of 1-dodecyl phenyl telluride (0.198 g, 0.52 mmol) and commercial chloramine-T trihydrate (0.300 g, 1.0 mmol) in THF (5 mL) is refluxed for 40 min under Nj. After evaporation of the solvent, the residue is treated with hexane (20 mL), and then fdtered. The filtrate is passed through a short Si02 column with hexane, giving, after evaporation, 1-dodecene as a colourless oil (0.068 g (78%)). 

Chloramine-T trihydrate (CT) was obtained commercially. Excess chloramine-T is used because we have observed traces of the a-ketosul-fonamide in those cases where the oxyaminated product contains a secondary hydroxyl group. We have also observed that these ct-ketosulfon-amides are further oxidized under the reaction conditions in a process which consumes several moles of chloramine-T. 

Chloramine-T trihydrate p-Toluenesulfonamide, A-chloro-, sodium salt (8) Benzenesulfonamide, A-chloro-4-methyl-, sodium salt, trihydrate (9) (7080-50-4)... 

Form Supplied in (1) white solid commercially available. Preparative Methods excess DMSO containing Copper(II) Chloride (or another copper catalyst) is treated with Chloramine-T trihydrate. (1) is obtained in 90% yield after aqueous EDTA workup and recrystallization from ethanol.The other A-tosylsulfoximines can be prepared by the tosylation of N-H sul-foximines with p-Toluenesulfonyl Chloride in the presence of base, but the two most useful and general methods are the oxidation of Af-tosylsulfilimines with basic Hydrogen Peroxide, ... 

The most common nitrogen sources used are aU N-halogenated species. The first modification reported by Sharpless and coworkers employed chloramine-T trihydrate (TsNClNa.3H20) as the nitrogen source. Subsequently, alternative reagents... 

Form Supplied in (1) white solid commercially available. Preparative Methods excess DMSO containing copper(II) chloride (or another copper catalyst) is treated with chloramine-T trihydrate. (1) is obtained in 90% yield after aqueous EDTA workup and recrystallization from ethanol. 

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