Summary
The synthesis and characterization of linear mono- and ditelechelic polyisobutylenes (PIBs) carrying terminal primary aldehyde groups are described. The synthesis starts by chlorine terminated PIBs (PIB−Cl and Cl−PIB−Cl) prepared by inifering or living carbocationic polymerization. These starting materials were dehydrochlorinated to vinylidene (∼CH2−C(CH3)=CH2) terminated PIBs and hydroformylated with CO/H2 in the presence of a rhodium catalyst. According to NMR (500 MHz) and GPC analyses, the transformations are selective and demonstrably quantitative. The structures of these novel polymers are:
I view of the rich chemistry of the aldehyde group, these materials are valuable intermediates.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J. P. Kennedy and R. A. Smith, Polym. Prepr., 20(2), 316 (1979).
R. Faust and J. P. Kennedy, Polym. Bull., 15, 317 (1986).
J. P. Kennedy and B. Iván, “Designed Polymers by Carbocationic Macromolecular Engineering: Theory and Practice”, Carl Hanser Verlag: Munich, 1992.
J. P. Kennedy, V. S. C. Chang, R. A. Smith, and B. Iván, Polym. Bull., 1, 575 (1979).
J. K. Stille in: “Comprehensive Organic Synthesis”, B. M. Trost, Ed.; Pergamon Press: Oxford, 1991; v. 4, p. 913.
M. Di Serio, R. Garaffa, and E. Santacesaria, J. Molec. Catal., 69, 1 (1991)
R. D. W. Kemmitt and D. R. Russell in: “Comprehensive Organometallic Chemistry”, Sir G. Wilkinson, F. G. A. Stone, and E. W. Abel, Eds.; Pergamon Press: Oxford, 1982; v. 5, p.36.
G. Kaszas, J. E. Puskas, J. P. Kennedy, and C. C. Chen, J. Macromol. Sci.-Chem., A26, 1099 (1989).
J. P. Kennedy and R. A. Smith, J. Polym. Sci., Polym. Chem. Ed., 18, 1523 (1980).
J. Chatt and L. M. Venanzi, J. Chem. Soc., 4735 (1957).
C. F. Baranauckas and I. Gordon, US Patent 3,511,857 (1970).
B. L. Goodall and P. A. M. Grotenhuis, US Patent 4,680,168 (1987). Chem. Abstr. 106:160024w (1987).
P. W. N. M. van Leeuwen and C. F. Roobeek, J. Organomet. Chem., 258, 343 (1983).
S. L. Manatt, J. D. Ingham, and J. A. Miller, Jr., Organic Magn. Reson. 10, 198 (1977).
B. Iván, J. P. Kennedy, and V. S. C. Chang, J. Polym. Sci., Polym. Chem. Ed., 18, 3177 (1980).
C. J. Pouchert, “The Aldrich Library of NMR Spectra”, 2nd ed, Aldrich Chemical Co.: Milwaukee, 1983; v. 1, p. 358.
J. March, “Advanced Organic Chemistry: Reactions, Mechanisms, and Structure”, 4th ed, John Wiley & Sons: New York, 1992.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lubnin, A.V., Kennedy, J.P. & Goodall, B.L. Synthesis and characterization of aldehyde-capped polyisobutylenes. Polymer Bulletin 30, 19–24 (1993). https://doi.org/10.1007/BF00296229
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00296229