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Issue 7, 2015
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Poly(phosphonate)-mediated Horner–Wadsworth–Emmons reactions

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Abstract

A novel, general protocol for a polymer-mediated Horner–Wadsworth–Emmons (HWE) reaction is reported. The polyvalent polymeric reagent was prepared via acyclic diene metathesis (ADMET) polymerization. Homo- and copolymers of reactive poly(phosphonate)s with molecular weights up to 40 000 g·mol−1 and molecular weight dispersities Đ < 2 were successfully synthesized. Subsequent application of these polymers in the HWE reaction to prepare a library of aromatic α,β-unsaturated ketones (chalcons) has proven to be an efficient synthetic pathway to minimize purification efforts, as the polymeric side-product can be removed by simple precipitation. In this paper we also demonstrate for the first time the preparation of a linear polyphosphate from a polyalkylphosphonate.

Graphical abstract: Poly(phosphonate)-mediated Horner–Wadsworth–Emmons reactions

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Publication details

The article was received on 06 Oct 2014, accepted on 13 Nov 2014 and first published on 13 Nov 2014


Article type: Paper
DOI: 10.1039/C4PY01365D
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Polym. Chem., 2015,6, 1192-1202

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    Poly(phosphonate)-mediated Horner–Wadsworth–Emmons reactions

    T. Steinbach, C. Wahlen and F. R. Wurm, Polym. Chem., 2015, 6, 1192
    DOI: 10.1039/C4PY01365D

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