Synthetic application of poly[styrene(iodoso diacetate)]

Synlett

Volumn , Issue 5, 1998, Pages 534-536

  Togo, Hideo ^a   Nogami, Genki ^a   Yokoyama, Masataka ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003115609     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1713     Document Type: Article

References (29)

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14. preparation of poly[styrene(iodoso difluoride)] and its synthetic use: Zupan, M.; Pollak, A. J. Chem. Soc., Chem. Commun., 1975, 715.
15. Iodination of polystyrene: A mixture of 16g of polystyrene, 16g of iodine, 6g of iodine pentoxide, 40 ml of carbon tetrachloride, and 30 ml of 50% sulfuric acid in 200 ml of nitrobenzene was kept at 90°C for 40 h. After the reaction, the reaction mixture was diluted with 100 ml of chloroform and then the precipitation occurred by the addition of methanol (1500 ml). The precipitates were collected by filtration. Elemental analysis showed C, 44.20%; H, 3.24%; I, 52.07%. This result indicates that 88% of the phenyl ring in polystyrene was iodinated. Preparation of Poly[styrene(iodoso diacetate)]: Hydrogen peroxide (30%, 40 ml) was added dropwise to acetic anhydride solution (145 ml) at 0°C. The solution was slowly warmed to room temperature, and stirred overnight. To this solution, poly(iodostyrene) (8g) was added. Then, the solution was kept at 40°C overnight. At the end of the reaction, ether was added to precipitate and the product was collected by filtration. Elemental analysis showed that C, 39.46%; H, 3.57%; I, 38.43%. This result indicates that 78% of the iodophenyl ring in poly(iodostyrene) was converted to the (diacetoxyiodo)phenyl ring.
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24. 4. The solvent was evaporated off under reduced pressure and the residue was purified by preparative TLC on silica gel.
25. All the compounds gave satisfactory spectroscopic and microanalytical data.
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29. Elemental analysis of recovered poly(iodostyrene) showed C, 44.32%; H, 3.42%; I, 51.63%. This result indicates that the number of the iodine group in poly(iodostyrene) was the same as in the initial state (88%). Elemental analysis of regenerated poly[styrene(iodoso diacetate)] showed C, 38.41%; H, 3.72%; I, 39.06%. This result indicates again that 64% of the iodophenyl ring in poly(iodostyrene) was converted to the (diacetoxyiodo)phenyl ring.