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Issue 86, 2015
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Poly(ω-bromoalkylnorbornenes-co-norbornene) by ROMP-hydrogenation: a robust support amenable to post-polymerization functionalization

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Abstract

The ring opening metathesis copolymerization of norbornene and ω-bromoalkylnorbornenes NB–(CH2)nBr (n = 1, 4) by Grubbs' 2nd generation catalyst, followed by hydrogenation, gives insoluble saturated polynorbornenes (ROMPH-PNBs) that have pendant ω-bromoalkyl chains (4a, b). These materials can be functionalized by nucleophilic substitution of bromide to give a variety of substituted polymers (ROMPH-PNB–(CH2)nNu where Nu = CN, SPh, OOCMe, N3, SnR3. The stannylated polymers were tested in a Pd-catalyzed reaction, the Stille coupling. The azido polynorbornenes ROMPH-PNB–(CH2)nN3 easily undergo the click 1,3-dipolar cycloaddition with alkynes, which could be a useful strategy to anchor other functionalities of interest. The aliphatic nature of the ROMPH-PNB–(CH2)nBr backbone makes robust supports and the presence of the bromo substituent imparts versatility so they are good candidates to be used as a general starting material to anchor a group required for a specific synthetic purpose.

Graphical abstract: Poly(ω-bromoalkylnorbornenes-co-norbornene) by ROMP-hydrogenation: a robust support amenable to post-polymerization functionalization

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Supplementary files

Article information


Submitted
27 Mar 2015
Accepted
04 Aug 2015
First published
10 Aug 2015

RSC Adv., 2015,5, 70244-70254
Article type
Paper
Author version available

Poly(ω-bromoalkylnorbornenes-co-norbornene) by ROMP-hydrogenation: a robust support amenable to post-polymerization functionalization

R. García-Loma and A. C. Albéniz, RSC Adv., 2015, 5, 70244
DOI: 10.1039/C5RA15187B

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