POLYMER-BOUND SULFONYLHYDRAZINE FUNCTIONALITY - PREPARATION, CHARACTERIZATION, AND REACTIONS OF COPOLY(STYRENE-DIVINYLBENZENESULFONYLHYDRAZINE)

A resin has been prepared which consists of a porous highly cross-linked polystyrene-divinylbenzene matrix functionalized with sulfonylhydrazine groups in the range of 0.8-5.2 mmol/g. The quantity of functional group can be determined by measuring the amount of nitrogen evolved when the resin is treated with sodium hypochlorite. The resin reacts with aldehydes, ketones, and glucose presumably to form the sulfonylhydrazone derivatives. The extent of reaction with ketones is sensitive to the bulk of the ketone, ranging from >90% with acetone to <2% with camphor. Both ketones and aldehydes can be displaced from the resin by pyruvic acid. On heating, the resin evolves diimide which hydrogenates the carbon-carbon double bond in alkenes additionally functionalized by a sulfide gr oup, a carboxyl group, or a carbonyl group. Deuteration of the double bond occurs when the reaction is carried out in the presence of deuterium oxide or polymer with deuterated hydrazine groups as shown by the formation of benzyl 2, 3-dideuteriopropyl sulfide from allyl benzyl sulfide and threo-2, 3-dideuterio-3-phenylpropanoic acid from trans-cinnamic acid. Monodeuterated products were also formed. Spent polymer which has been used for diimide generation can be recycled to regenerate resin in the sulfonylhydrazine form. © 1979, American Chemical Society. All rights reserved.