Journal
TETRAHEDRON
Volume 61, Issue 51, Pages 12160-12167Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.08.121
Keywords
organic synthesis; cross-linked polystyrene; macromonomers
Categories
Ask authors/readers for more resources
Cross-linked polystyrene (PS) with polytetrahydrofuran (PTHF) chains were prepared for use in solid phase organic synthesis (SPOS). The resins were prepared from styrene, styrene-PTHF macromonomers and cross-linkers 1,4-bis [4-vinylphenoxyl]butane or divinylbenzene by suspension polymerization. The styrene-PTHF macromonomers were prepared by cationic polymerization of 4-vinylbenzyl bromide and 4-(4-vinylphenoxy)butyl iodide activated by silver hexafluoroantimonate and 4-(5-hydroxypentyl) styrene activated by triflic anhydride. Alternatively, polytetrahydrofuran-grafted polystyrene (PS-PTHF) resins could also be directly prepared from 5-hydroxypentyl JandaJel by cationic polymerization using triflic anhydride as the initiator. These PS-PTHF resins exhibited good swelling characteristics across a wide spectrum of polar and non-polar solvents. These resins were used in the synthesis of 3-methyl-1-phenyl-2-pyrazolin-5-one, which requires beta-ketoester formation at low temperature (-78 degrees C), resulting in good yield and product purity; whereas the same synthesis carried out on PEG-grafted PS (PS-PEG) resin resulted in incomplete synthesis. (c) 2005 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available