Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01365d
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...
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| creator | Steinbach, Tobias Wahlen, Christian Wurm, Frederik R |
| description | 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
< 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.
Poly(phosphonate)s were used in Horner-Wadsworth-Emmons (HWE) reactions with aldehydes. The progress of the reaction was monitored
via in situ
-NMR spectroscopy. Minimal purification efforts by precipitation of the polymer are achieved. |
| doi_str_mv | 10.1039/c4py01365d |
| format | Article |
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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
< 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.
Poly(phosphonate)s were used in Horner-Wadsworth-Emmons (HWE) reactions with aldehydes. The progress of the reaction was monitored
via in situ
-NMR spectroscopy. Minimal purification efforts by precipitation of the polymer are achieved.</description><identifier>ISSN: 1759-9954</identifier><identifier>EISSN: 1759-9962</identifier><identifier>DOI: 10.1039/c4py01365d</identifier><language>eng</language><creationdate>2015-02</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Steinbach, Tobias</creatorcontrib><creatorcontrib>Wahlen, Christian</creatorcontrib><creatorcontrib>Wurm, Frederik R</creatorcontrib><title>Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01365d</title><description>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
< 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.
Poly(phosphonate)s were used in Horner-Wadsworth-Emmons (HWE) reactions with aldehydes. The progress of the reaction was monitored
via in situ
-NMR spectroscopy. Minimal purification efforts by precipitation of the polymer are achieved.</description><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjk9LAzEUxIMoWGovvQvx1h5SN83uynrVlfakUMHjkiZvaST_SKKyH6Lf2QhSD4X6YHg_mGEYhKa0WNCCNbei9ENBWV3JMzSid1VDmqZenh-4Ki_RJMb3Ih-j5ZLVI7R_cXqY-Z2LWZYnmBMDUmWQeOWChUDeuIxfLqQdaY1xNuIAXCSVqdUgUnBWCRw_vNdgwCYeBqxs74LhPyE8azfrOeafXGm-1bDAGwD8-Ly-x8e7r9BFz3WEye8fo-un9vVhRUIUnQ_K5PLuL87G6OaU33nZs_86vgH2yGGI</recordid><startdate>20150203</startdate><enddate>20150203</enddate><creator>Steinbach, Tobias</creator><creator>Wahlen, Christian</creator><creator>Wurm, Frederik R</creator><scope/></search><sort><creationdate>20150203</creationdate><title>Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01365d</title><author>Steinbach, Tobias ; Wahlen, Christian ; Wurm, Frederik R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c4py01365d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Steinbach, Tobias</creatorcontrib><creatorcontrib>Wahlen, Christian</creatorcontrib><creatorcontrib>Wurm, Frederik R</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Steinbach, Tobias</au><au>Wahlen, Christian</au><au>Wurm, Frederik R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01365d</atitle><date>2015-02-03</date><risdate>2015</risdate><volume>6</volume><issue>7</issue><spage>1192</spage><epage>122</epage><pages>1192-122</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><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
< 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.
Poly(phosphonate)s were used in Horner-Wadsworth-Emmons (HWE) reactions with aldehydes. The progress of the reaction was monitored
via in situ
-NMR spectroscopy. Minimal purification efforts by precipitation of the polymer are achieved.</abstract><doi>10.1039/c4py01365d</doi><tpages>11</tpages></addata></record> |
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| title | Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01365d |
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