TY - JOUR A1 - Sahoo, Dhananjaya A1 - Thiele, Susanne A1 - Schulte, Miriam A1 - Ramezanian, Navid A1 - Godt, Adelheid T1 - Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene)s and an update on the synthesis of oligoPPEs JF - Beilstein Journal of Organic Chemistry PY - 2010/// VL - 6 SP - 57 SN - 1860-5397 DO - 10.3762/bjoc.6.57 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.6.57 KW - alkyne protecting group KW - carbometalation KW - C–C coupling KW - phenyleneethynylene KW - polar tagging N2 - 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-MnO2 proved to be better than (highly) activated MnO2. 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. ER - TY - JOUR AU - Daniell, H. W. AU - Klotz, E. J. F. AU - Odell, B. AU - Claridge, T. D. W. AU - Anderson, H. L. JF - Angew. Chem. 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In this procedure less MnCl2 • 4 H2O (200 g vs. 220 g) but the same amount of KMnO4 (160 g) and of solvent was used in comparison to the procedure given in [64]. ER - TY - GEN N1 - As purchased; 80% technical grade. ER - TY - JOUR AU - Fatiadi, A. J. JF - Synthesis PY - 1987/// SP - 85 EP - 127 DO - 10.1055/s-1987-27859 ER - TY - JOUR AU - Firouzabadi, H. AU - Ghaderi, E. JF - Tetrahedron Lett. PY - 1978/// VL - 19 SP - 839 EP - 840 DO - 10.1016/S0040-4039(01)85412-5 ER - TY - GEN N1 - Experimental proof: Carbometalation product 5a was treated with γ-MnO2 and powdered KOH in diethylether at room temperature. The 1H NMR spectrum of the crude product shows unambigously the signals of the expected aldehyde 6a. There are no signals that fit to the characteristic signals of the unsymmetrically 1,1-disubstituted alkene 7, the product in case 6a had lost the formyl group. 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