Summary
Two novel reactive polymers useful as protecting groups for hydroxyls have been prepared by copolymerization of a silicon containing monomer, 4-[3′-(dimethyl phenyl silyl)-propyl]-styrene, with styrene and divinylbenzene, followed by chemical modification of the resulting insoluble polymer beads. The polymeric reagents containing trialkylsilyl chloride or trialkylsilyl trifluoroacetate moieties are effective for the protection of alcohols and a procedure for their facile regeneration is described.
Similar content being viewed by others
References
S.K. Chaudhary and O. Hernandez, Tetrahedron. Lett., 2 (1979) 99. M. Lalonde and T.H. Chan, Synthesis, (1985) 817.
T.H. Chan and W.-Q. Huang, J. Chem. Soc. Chem. Commun., (1985) 909.
D.C. Sherrington and P. Hodge (Editors) “Syntheses and separations using functional polymers”, J. Wiley and Sons, London (1988). W.T. Ford (Editor) “Polymeric reagents and catalysts” ACS Symposium Series #308 Washington, D.C. (1986).
J.M.J. Fréchet, Tetrahedron, (1981) 37, 663.
R.H. Lewis, U.S. Patent #2,500,761 (1950).
J.M.J. Fréchet and M.J. Farrall, in “Chemistry and Properties of Crosslinked Polymers”; (S.S. Labana, Editor) Academic Press (1977) 59.
G.D. Darling and J.M.J. Fréchet, J. Org. Chem. (1986) 51, 2270. J.M.J. Fréchet, G.D. Darling, S. Itsuno, P.Z. Lü, M. Vivas de Meftahi, and W.A. Rolls, Jr.: Pure Appl. Chem. (1988) 60, 353.
A. Deratani, G.D. Darling, D. Horak, J.M.J. Fréchet, Macromolecules (1987) 20, 767. A. Deratani, G.D. Darling, J.M.J. Fréchet, Polymer (1987) 28, 825.
E.L. Foreman and S.M. McElvain., J. Am. Chem. Soc., (1940) 62, 1435.
B.B. Snider, J. Org. Chem., (1973) 38, 3961.
C.G. Overberger and J.H. Saunders, Organic Syntheses, (1948) 28, 31.
R.M. Pike, J. Polym. Sci., (1959) XL(137) 577.
W.A. Rolls, Jr., F. Svec, and J.M.J. Fréchet, Polymer (1990) 31, 165.
C. Eaborn, J. Organomet. Chem., (1975) 100, 43 and references within. C. Eaborn, I.D. Jenkins and D.R.M. Walton, J.C.S. Perkin II, (1974) 596.
D. Häbich and F. Effenberger, Synthesis, (1978) 755.
A.J. Jones, C.C. Leznoff and P.I. Svirskaya., Org. Magn. Reson., (1982) 18 (4), 236.
L.A. Errede, R.A. Newmark and J.R. Hill, Macromolecules, (1986) 19, 651.
H.D.H. Stöver and J.M.J. Fréchet, Macromolecules (1989) 22, 1574.
H.D.H. Stöver and J.M.J. Fréchet, Macromolecules (1991) 24, in press.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Stöver, H.D.H., Lü, PZ. & Fréchet, J.M.J. Polymeric reagents: preparation and characterization of novel solid-phase, silylating agents derived from copolymers containing 4-[3′-(dimethyl phenyl silyl)-propyl]-styrene. Polymer Bulletin 25, 575–582 (1991). https://doi.org/10.1007/BF00293517
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00293517