Bromination and Lithiation: Two Important Steps in the Functionalization of Polystyrene Resins

M. Jean Farrall, Jean Frechet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

371 Scopus citations

Abstract

Reactions used for the bromination and lithiation of cross-linked polystyrene resins have been explored. In the presence of bromine and catalytic amounts of a thallium(III) salt, polystyrene resins are smoothly brominated and give homogeneous reactive resins with a highly reproducible degree of functionalization. These resins can be lithiated easily by reaction with an excess of n-butyllithium in benzene. Other swelling agents such as tetrahydrofuran gave incomplete removal of the bromine. The direct lithiation of polystyrene with n-butyllithium and tetramethylethylenediamine gave lithiated polymers containing approximately 2 mequiv of functional group per gram, while direct lithiation in the presence of triethylenediamine gave lower degrees of functionalization. The lithiated resins were used to prepare polymers containing carboxylic acid, thiol, sulfide, boronic acid, amide, silyl chloride, phosphine, alkl bromide, aldehyde, alcohol, or trityl functional groups for applications in polymer-assisted syntheses.

Original languageEnglish (US)
Pages (from-to)3877-3882
Number of pages6
JournalJournal of Organic Chemistry
Volume41
Issue number24
DOIs
StatePublished - Nov 1 1976

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Bromination and Lithiation: Two Important Steps in the Functionalization of Polystyrene Resins'. Together they form a unique fingerprint.

Cite this