Lithiation–alkylation of Polystyrene Occurs Only on the Ring

Authors

Thomas J. Xue, Marquette UniversityFollow
Mark S. Jones, The University - Lancaster
John R. Ebdon, The University - Lancaster
Charles Wilkie, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

2-1997

Publisher

Wiley

Source Publication

Journal of Polymer Science: Part A, Polymer Chemistry

Source ISSN

0887-624X

Abstract

When polystyrene is treated with an organolithium reagent, the hydrogen on the para carbon is removed and this position may be alkylated with e.g., iodomethane or chlorotrimethylsilane. The metalation occurs directly at this position and does not involve metalation at the benzylic carbon with resonance distribution of the charge to the ring. The reaction of cumene with butyllithium also occurs by direct ring metalation and it is shown that these results are consistent with both the kinetic and the thermodynamic acidity of the hydrocarbons.

Comments

Journal of Polymer Science: Part A, Polymer Chemistry, Vol. 35, No. 3 (February 1997): 509-513. DOI.

Recommended Citation

Xue, Thomas J.; Jones, Mark S.; Ebdon, John R.; and Wilkie, Charles, "Lithiation–alkylation of Polystyrene Occurs Only on the Ring" (1997). Chemistry Faculty Research and Publications. 768.
https://epublications.marquette.edu/chem_fac/768