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Exploiting Aggregation To Achieve Phase Separation in Macrocyclization
Author(s) -
Bédard AnneCatherine,
Collins Shawn K.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203433
Subject(s) - peg ratio , selectivity , chemistry , ethylene glycol , phase (matter) , yield (engineering) , solvent , chemical engineering , dilution , ethylene , catalysis , chromatography , organic chemistry , materials science , engineering , economics , metallurgy , thermodynamics , physics , finance
The aggregation properties of poly(ethylene glycol) (PEG) can be exploited in organic synthesis to control dilution effects. Through the use of solvent mixtures containing PEG 400 /MeOH, macrocyclization by Glaser–Hay coupling can be conducted at high concentrations. The origin of the selectivity has been studied by using surface tension measurements, UV spectroscopy, and chemical tagging and demonstrates the dependence of the yield and selectivity on the aggregation of PEG 400 and its ability to preferentially solubilize organic substrates, resulting in a phase separation from the catalyst system.