Solid-phase acylating reagents in new format: Macroporous polymer disks

Jennifer A. Tripp, Frantisek Svec, Jean M.J. Fréchet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Acylation resins in a new monolithic format have been prepared by the functionalization of polyethyleneencased porous poly(chloromethylstyrene-co-divinylbenzene) disks. These disks have been obtained from a monolithic rod prepared by polymerization in a cylindrical glass mold, then cut into a disk format. A free radical azo initiator 4,4′-azobis(4-cyanovaleric acid) attached to available chloromethyl functionalities at the surface of the pores was used to initiate graft polymerization of 4-acetoxystyrene or chloromethylstyrene from the surface. Addition of a small percentage of divinylbenzene to the polymerization mixture leads to the formation of a layer of swellable reactive polymer gel at the surface of the macropores. This both prevents the undesirable increase in flow resistance through the monolith and improves the yield of grafting. The final reaction steps involve formation of an active phenolic moiety grafted to the disks and its reaction with acid anhydride. The use of grafted disks as acylating resin to transform various amines to amides in flow-through operations is demonstrated in a variety of solvents including alcohols. The acylation ability of the depleted disks can easily be recovered, and the disks can be reused many times.

Original languageEnglish (US)
Pages (from-to)604-611
Number of pages8
JournalJournal of Combinatorial Chemistry
Volume3
Issue number6
DOIs
StatePublished - Nov 2001
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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