biphasic mixture of oil and solvent the ruthenium iii chloride 20 mg was added and the mixture stirred under argon the sodium periodate 67 4 g 0 32 mol was added in four equal portions no exotherm was seen after the addition this mixture was stirred at room temperature for two hours and product slowly crystallized from the reaction mixture this was filtered and dried overnight at 50 u00b0 c in a vacuum oven yield 94 6 g of tan solid 87 yield the filtrate was extracted with methyl t butyl ether and concentrated to give an additional 6 g of material for an overall yield of 93 1 h nmr cdcl 3 u03b4 7 8 d 4h 7 4 d 4h 5 0 m 2h 4 4 m 4h 3 0 br s 2h 2 5 s 6h ______________________________________8 str53 chemical mw density scale factor______________________________________cyclic sulfate 6 492 5 1 equiv sodium azide 65 01 1 15 equiv acetone 58 08 791 1 g 6 5 mldi water 18 1 1 g 6 8 ml______________________________________ the cyclic sulfate 545 4 g 1 10 moles was dissolved in 2500 ml of acetone and 500 ml of water no ppt present while stirring at ambient temperature sodium azide 1 21 moles 1 1 equiv 78 6 g was added in four portions over 10 minutes no temperature rise was observed the reaction was followed by hplc after 24 hours hplc indicated that the reaction contained 5 starting material and a single major product another 5 g of nan 3 was added and the reaction was allowed to stir another 18 hours.