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Quantitative amine functionalization of polymeric organolithium compounds with 3-dimethylaminopropyl chloride in the presence of lithium chloride

✍ Scribed by Roderic P. Quirk; Youngjoon Lee

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 141 KB
Volume: 38
Category: Article
ISSN: 0887-624X
DOI: 10.1002/(sici)1099-0518(20000101)38:1<145::aid-pola19>3.0.co;2-6

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✦ Synopsis

The addition of lithium chloride promoted the coupling reaction of hydrocarbon solutions of poly(styryl)lithium (PSLi) and poly(isoprenyl)lithium (PILi) with 3-dimethylaminopropyl chloride to form the corresponding -dimethylamino-functionalized polymers. Quantitative amine functionalization was achieved for PSLi and PILi in the presence of 1 and 10 equivalents, respectively, of LiCl in benzene; the functionalization efficiency was only 67% for PSLi and 85% for PILi in the absence of LiCl. The polymer products were characterized by size exclusion chromatography, thin-layer chromatography, and amine end-group titration. The pure amine-functionalized polymers were isolated by silica gel column chromatography.

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