Tosyl azide, polymer-supported

Alternate Name polystyrene-supported benzenesulfonyl azide, PS-TsA. 

Physical Data white polymer beads, 100-200 mesh, loading of 1.0-1.5 mmol/g, initiation temperature is 130 °C, onset temperature is 165.98 °C, peak exotherm is 192.72 °C, heat of decomposition is 0.27 cal/s/g, and BAM friction 360 N. 

Form Supplied in polystyrene-supported beads of 100-200 mesh and 1.0-1.5 mmol/g loading. 

Analysis of Reagent Purity Fourier transform infrared spectroscopy (FTIR), combustion analysis. 

Preparative Methods the title reagent can be prepared in one step by the reaction of polystyrene-supported benzenesulfonyl chloride (100-200 mesh, available from Aldrich, 51,623-6 [163894-16-4], as 1% DVB cross-linked polystyrene resin with a loading of 1.5-2.0 mmol/g) with sodium azide (1.5 equiv) in DMF/H2O (reaction complete at rt in 16 h). 

---

Polymer-supported Reagents. Polymer-supported toluene-sulfonyl azide I3I was prepared by reaction of a macroreticular p-toluenesulfonyl chloride resin (prepared, in turn, by chlorosul-fonation of Amberlite XE 305) with excess sodium azide. Resin 13, a solid-phase equivalent of />-toluenesulfonyl azide, can be used for diazo transfer to /3-dicarbonyl compounds (eq 14). Unlike tosyl azide, resin 13 does not detonate on shock treatment and is stable at room temperature. Recently, an analogous benzenesul-fonyl azide resin has been prepared from PS-TsCl. ... 

---