Citation:
SYNTHESIS AND CATIONIC RING-OPENING POLYMERIZATION OF 1, 4-ANHYDRO-2, 3-DI-O-(P-AZIDOBENZYL)-α-D-RIBOPYRANOSE[J]. Chinese Journal of Polymer Science,
1999, 17(2): 123-128.
SYNTHESIS AND CATIONIC RING-OPENING POLYMERIZATION OF 1, 4-ANHYDRO-2, 3-DI-O-(P-AZIDOBENZYL)-α-D-RIBOPYRANOSE
摘要:
New highly stereoregular 2, 3 -di- O-(p-azidobenzyl )-(1 →5 ) - α-D -ribofuranan was synthesized byselective ring-opening polymerization of 1, 4-anhydro-2, 3 - di-O -(p-azidobenzyl )-α-D -ribopyranose(ADABR) using phosphorus pentafluoride or tin tetrachloride as catalyst at low temperature indichloromethane. The monomer was obtained by the reaction of p - bromomethyl -phenyleneazide with 1, 4 -anhydro-α-D-ribose in DMF. The structure of poly(ADANR) was identified by specific rotation and 13C-NMR spectroscopy.Acid chloride-AgCl4 complex catalyst such as CH2=C(CH3)C+OClO4- used in the polymerization resulted in polymers with mixed stryctures,i.e.(1→5)-α-D-ribofuranosidic and (1→4)-β-D-ribopyranosidic units.However,with C6H5C+OClO4- as catalyst,pure(1→5)-α-D-ribofuranan was obtained.The effects of catalyst,polymerization temperature and time on polymer stereoregularity were examined,and the mechanism of the ring-opning polymerization was discussed.
English
SYNTHESIS AND CATIONIC RING-OPENING POLYMERIZATION OF 1, 4-ANHYDRO-2, 3-DI-O-(P-AZIDOBENZYL)-α-D-RIBOPYRANOSE
Abstract:
New highly stereoregular 2, 3 -di- O-(p-azidobenzyl )-(1 →5 ) - α-D -ribofuranan was synthesized byselective ring-opening polymerization of 1, 4-anhydro-2, 3 - di-O -(p-azidobenzyl )-α-D -ribopyranose(ADABR) using phosphorus pentafluoride or tin tetrachloride as catalyst at low temperature indichloromethane. The monomer was obtained by the reaction of p - bromomethyl -phenyleneazide with 1, 4 -anhydro-α-D-ribose in DMF. The structure of poly(ADANR) was identified by specific rotation and 13C-NMR spectroscopy.Acid chloride-AgCl4 complex catalyst such as CH2=C(CH3)C+OClO4- used in the polymerization resulted in polymers with mixed stryctures,i.e.(1→5)-α-D-ribofuranosidic and (1→4)-β-D-ribopyranosidic units.However,with C6H5C+OClO4- as catalyst,pure(1→5)-α-D-ribofuranan was obtained.The effects of catalyst,polymerization temperature and time on polymer stereoregularity were examined,and the mechanism of the ring-opning polymerization was discussed.
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