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Selective O‐allylation of bisphenol A: toward a chloride‐free route for epoxy resins
Author(s) -
van Rijn Jimmy A.,
Guijt Marieke C.,
Bouwman Elisabeth,
Drent Eite
Publication year - 2011
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.1743
Subject(s) - chemistry , selectivity , catalysis , bisphenol a , bisphenol , ether , organic chemistry , solvent , epoxy , chloride , phenols , ruthenium , vinyl chloride , epoxide , polymer , copolymer
The O‐allylation of bisphenol A (BPA) has been performed with the most selective catalysts for O‐allylation of phenols reported previously. Both the cyclopentadienyl–ruthenium catalysts and the palladium–diphosphine catalysts are capable of selectively performing single and double O‐allylation of BPA. An intriguing solvent effect is observed; the choice of the solvent is of key importance for both conversion and selectivity. The use of an excess of diallyl ether as allylating agent results in relatively high yields of the bisallyl ether of bisphenol A, while maintaining the high selectivity for O‐allylation. Copyright © 2010 John Wiley & Sons, Ltd.