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Issue 8, 2000
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Poly(N-vinylpyrrolidinone) (PNVP) bearing 5-fluorouracil (5-FU) moieties was synthesised via a three-step method. Firstly, 5-FU reacted with formaldehyde to form a mixture of mono- and disubstituted hydroxymethyl-5-FUs. The mixture was then treated with allyl chloroformate to afford allyloxycarbonyloxymethyl-5-FUs. This reaction showed site-specificity: the hydroxymethyl goup at the N-1 position readily reacted with chloroformate whereas the N-3 hydroxymethyl group partially decomposed into formaldehyde and the amide group. 1-Allyloxycarbonyloxymethyl-5-FU (4) and NVP were copolymerized in dioxane using azobisisobutyronitrile as an initiator. The monomer reactivity ratios, r4 = 0.32 and rNVP = 0.97, were evaluated by both linear and non-linear methods.

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Article information

15 Mar 2000
17 May 2000
First published
03 Jul 2000

J. Mater. Chem., 2000,10, 1771-1775
Article type

Synthesis of allyloxycarbonyloxymethyl-5-fluorouracil and copolymerizations with N-vinylpyrrolidinone

Z. Liu, N. Fullwood and S. Rimmer, J. Mater. Chem., 2000, 10, 1771
DOI: 10.1039/B002092N

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