Abstract
Polystyrene supported oximino dithiocarbonic anhydrides are a new class of regenerable solid phase reagents for acylating amino groups selectively. The reagent was prepared by a series of polymer analogous reactions starting from 2% DVB crosslinked polystyrene resin. Polystyrene resin was converted to the aldehyde or keto resin and then to the oxime resin. Reaction of the oxime resin with carbon disulphide and aqueous sodium hydroxide gave a dithiocarbonate resin. Treatment of this resin with an acyl chloride gave the oximino dithiocarbonic anhydride resin. The insoluble anhydrides were found to transfer the acyl groups to amines in solution at room temperature, yielding a solution of the corresponding amide. The spent reagent can be regenerated to the oximino dithiocarbonic anhydride by a simple reaction, without considerable loss in activity.
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