Abstract
Polymeric organocalcium reagents were prepared via the oxidative addition of highly reactive calcium, prepared from the lithium biphenylide reduction of calcium iodide, to cross-linkedp-bromopolystyrene,p-chloropolystyrene,p-fluoropolystyrene, and chloromethylated polystyrene. These organocalcium reagents react with a variety of electrophiles to yield functionalized polymers.
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For reviews concerning the functionalization of polymers and their use, see D. C. Sherrington and P. Hodge (eds.),Synthesis and Separations Using Functional Polymers (John Wiley and Sons, New York, 1988), pp. 43–122, and references cited therein.
S. Itsuno, G. D. Darling, H. D. H. Stöver, and J. M. J. Fréchet,J. Org. Chem. 52, 4645 (1987), and references cited therein.
S. Harvey and C. L. Raston,J. Chem. Soc. Chem. Commun. 10, 652 (1988).
S. Itsuno, G. D. Darling, P. Z. Lu, and J. M. J. Fréchet,J. Polym. Mater. Sci. Eng. 57, 570 (1987).
R. A. O'Brien and R. D. Rieke,J. Org. Chem. 55, 788 (1990).
R. D. Rieke,Science 246, 1260 (1989).
T. C. Wu, H. Xiong, and R. D. Rieke,J. Org. Chem. 55, 5045 (1990).
Functional yield for the carboxylated polymer was based on acid-base titration: (a) L. C. Anand, A. Takahasi, and N. G. Gaylord,Macromol. Symp. 4, 9 (1972).
Functional yield for the carboxylated polymer was based on acid-base titration: (b) See Ref. 6.
M. J. Farrall and J. M. J. Fréchet,J. Org. Chem. 41, 3877 (1976), and references cited therein.
Polymers prepared by known literature procedures: L. R. Melby and D. R. Strobach,J. Am. Chem. Soc. 89, 450 (1967).
R. D. Rieke and S. E. Bales,J. Am. Chem. Soc. 96, 1775 (1974).
S. H. Yu and E. C. Ashby,J. Org. Chem. 36, 2123 (1971), and references cited therein.
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O'Brien, R.A., Chen, Ta. & Rieke, R.D. Functionalization of halogenated polystyrene resins utilizing highly reactive calcium. J Inorg Organomet Polym 2, 345–356 (1992). https://doi.org/10.1007/BF00777251
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DOI: https://doi.org/10.1007/BF00777251