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Anionic synthesis and characterization of ω-carboaldehyde-functionalized polybutadienes and polyisoprenes

✍ Scribed by Roderic P. Quirk; Jianxin Kuang

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
313 KB
Volume
37
Category
Article
ISSN
0887-624X

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✦ Synopsis

Attempted preparation of -formyl-functionalized polydienes by termination of poly(butadienyl)lithium and poly(isoprenyl)lithium with 4-morpholinecarboaldehyde resulted in 73 and 38% dimer formation (SEC), respectively, under conditions that quantitativey produced -formyl-functionalized polystyrene. Dimer formation was attributed to postfunctionalization, base-catalyzed, aldol-type condensation based on FTIR and 1 H-NMR analysis of the dimer products. High yields (Ͼ97%) of -formylfunctionalized polydienes were formed by workup using acidic methanol; quantitative functionalization resulted from end capping the polymeric organolithium chain ends with 1,1-diphenylethylene prior to the functionalization reaction. The -formylpolydienes were characterized by hydroxylamine end-group titration, FTIR, and both 1 Hand 13 C-NMR spectroscopy.

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