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Organotin catalysts grafted onto cross‐linked polystyrene supports through polar spacers
Author(s) -
Pinoie Vanja,
Biesemans Monique,
Willem Rudolph
Publication year - 2010
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1578
Subject(s) - chemistry , transesterification , catalysis , polystyrene , ethylene glycol , alkyl , linker , polymer chemistry , peg ratio , organic chemistry , combinatorial chemistry , polymer , finance , computer science , economics , operating system
The present study investigates the suitability of a HypoGel support bearing oligomeric poly(ethylene glycol) (PEG) chains to act as an insoluble carrier for grafted organotin catalysts. Through the introduction of polar spacers, an improved swelling and site accessibility in the polar media typically involved in transesterification reactions are targeted. Advanced structural investigation shows that quantitative conversion into the targeted HypoGel‐supported organotin trichloride is hampered by the existence of intra‐ and/or intermolecular donor‐acceptor O→Sn interactions caused by the presence of donor moieties in the PEG‐linker. Support is provided to the proposal that the latter interactions are at the origin of the moderate catalytic performance displayed by these HypoGel‐supported catalysts, achieving only 41% conversion after 2 hours in the transesterification of ethyl acetate and n ‐octanol. In contrast with similar organotin catalysts supported by an alkyl spacer, the HypoGel‐supported materials appear to be poorly recyclable and display poor leaching resistance. Copyright © 2009 John Wiley & Sons, Ltd.