2-hydroxyethyl methacrylate; turbidity titration A solution of 1.223 g (8.06 mmol) of chloromethylstyreach 100% because of the presence of chain transfer rene, 7.512 g (72.1 mmol) of styrene, and 0.397 g (2.42 reaction. 4 We now propose that graft polymer can be mmol) of AIBN in 80 mL of chlorobenzene was degassed effectively obtained by utilization of a good chain transand heated at 60ะC for 24 h in sealed tube. The reaction fer function. If chain transfer constant to the polymer mixture was poured into 1 L of methanol. The precipiis high enough, the termination occurs mainly by the tate was isolated by filtration, washed thoroughly with chain transfer on the polymer, and the graft chain methanol, and dried under reduced pressure. The crude grows from the resulting radical without the formation polymer was dissolved in dichloromethane, and repreof homopolymer. 2 cipitated in methanol to give 7.949 g of copoly(chloro-Among the many chain transfer reagents, mercapmethylstyrene-styrene). tan and disulfide were extensively utilized. Although a polymer bearing mercapto group rapidly undergoes oxidative crosslinking, grafting onto proteins, such as Allyl Benzyl Sulfide (1) wool and silk, has been investigated using mercapto group of cysteine. 5 Further, radical polymerization in the presence of a polymer bearing disulfide group may
In distillation instrument under nitrogen atmosphere, a solution of 207 mg (1.63 mmol) of benzyl chloride and afford considerable amount of homopolymer and crosslinked polymer because regioselectivity of radical at-491 mg (3.23 mmol) of DBU in 4 mL of THF was placed in receiver vessel, and ca. 4 g of allyl mercaptan was tack on disulfide is generally low.
We attended allylthio group as a chain transfer placed in distillation vessel. The receiver vessel was kept in dark. With stirring receiver vessel, allyl mer-group. Allylthio group is inert to oxygen and water, and a radical selectively attacks g-position of allylthio captan was distilled under atmospheric pressure. The distillation was completed within 10 min, and the reac-group to afford thiyl radical via the fission of C{S bond. [6][7][8] Further, allylthio group is expected to be easily tion mixture was allowed to stir for an additional 20 min. The reaction mixture was diluted by 30 mL of introduced into the polymer by the polymer reaction of chloromethylstyrene and allyl mercaptan. In this com-ethyl acetate, washed with water, hydrochloric acid (1 mol/L), followed by brine, and was dried with sodium sulfate. After volatiles were removed in reduced pres-
Correspondence to: T. Fukutomi sure, crude allyl benzyl sulfide was obtained as a color-