Functionalization of Reactive Polymers by Metalation with Superbases followed by Reaction with Electrophiles.
Abstract
In order to test novel routes for the functionalization of polyolefins, hydrocarbon-soluble superbases have been used for the selective metalation of a copolymer of isobutylene and p- methylstyrene. The metalation reaction directed at the benzylic p-methyl position is followed by (1)H NMR spectrometry after quenching with an electrophile. Superbases obtained by the procedure of Lochmann involving the reaction of butyl lithium with a heavier alkali alkoxide have a reactivity that increases with the size of the metal cation. Best results are obtained using a superbase derived from s-BuLi and cesium l-(-)-menthoxide in the ratio of 1:3. Complete metalation of all the benzylic p-methyl groups is possible if an excess of superbase is used. This method of functionalization developed for solutions of the poly(isobutylene-co-p-methylstyrene) rubbers may also be applicable to introduce functional groups onto surfaces.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 30, 1996
- Accession Number
- ADA310761
Entities
People
- Jean Fréchet
- Joachim H. Steinke
- Kenneth J. Wynne
- Shah A. Haque
Organizations
- Cornell University