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- W2113670662 abstract "One important access to monodisperse (functionalized) oligoPPEs is based on the orthogonality of the alkyne protecting groups triisopropylsilyl and hydroxymethyl (HOM) and on the polar tagging with the hydroxymethyl moiety for an easy chromatographic separation of the products. This paper provides an update of this synthetic route. For the deprotection of HOM protected alkynes, γ-MnO 2 proved to be better than (highly) activated MnO 2 . The use of HOM as an alkyne protecting group is accompanied by carbometalation as a side reaction in the alkynyl–aryl coupling. The extent of carbometalation can be distinctly reduced through substitution of HOM for 1-hydroxyethyl. The strategy of polar tagging is extended by embedding ether linkages within the solubilising side chains. With building blocks such as 1,4-diiodo-2,5-bis(6-methoxyhexyl) less steps are needed to assemble oligoPPEs with functional end groups and the isolation of pure compounds becomes simple. For the preparation of 1,4-dialkyl-2,5-diiodobenzene a better procedure is presented together with the finding that 1,4-dialkyl-2,3-diiodobenzene, a constitutional isomer of 1,4-dialkyl-2,5-diiodobenzene, is one of the byproducts." @default.
- W2113670662 created "2016-06-24" @default.
- W2113670662 creator A5006667557 @default.
- W2113670662 creator A5044803977 @default.
- W2113670662 creator A5056159574 @default.
- W2113670662 creator A5061647750 @default.
- W2113670662 creator A5075227883 @default.
- W2113670662 date "2010-06-01" @default.
- W2113670662 modified "2023-10-16" @default.
- W2113670662 title "Polar tagging in the synthesis of monodisperse oligo(<i>p</i>-phenyleneethynylene)s and an update on the synthesis of oligoPPEs" @default.
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- W2113670662 doi "https://doi.org/10.3762/bjoc.6.57" @default.
- W2113670662 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2900939" @default.
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- W2113670662 hasPublicationYear "2010" @default.
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