Cleavage and Coupling of Bis(4-vinylbenzyl)disulfide as a Novel Cross-linker for Reversible Solubilizing Polystyrene Supports

抄録

A polystyrene cross-linked with disulfide moiety was prepared from copolymerization of styrene with bis(4-vinylbenzyl)disulfide (1) under suspension conditions. The obtained copolymer was treated with tributylphosphine in THF at rt and the resulting linear copolymer dissolved completely in THF by reduction of disulfides into thiols. Then, acetyl capping was done for the thiol resin to maintain its solubility by avoiding the coupling of thiols. Further this resin was turned insoluble again by consecutive uncapping of thioester to thiol using NaBH4 in EtOH/THF at rt, and recoupling of thiol by treating with I2 in toluene at rt. The reaction conditions of cleavage and recouple of disulfide bond were thoroughly investigated.