Asymmetric anionic polymerization of 7-cyano-7-phenyl-1,4-benzoquinone methide
Asymmetric anionic polymerizations of a prochiral monomer, 7-cyano-7-phenyl-1,4-benzoquinone methide ( 3 ), using chiral initiators were performed under various conditions, and optically active polymers having configurational chirality in the main chain were obtained though their specific rotation v...
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| Veröffentlicht in: | Polymer bulletin (Berlin, Germany) Germany), 2012-04, Vol.68 (7), p.1831-1844 |
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| container_issue | 7 |
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| container_title | Polymer bulletin (Berlin, Germany) |
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| creator | Nakagawa, Risa Uno, Takahiro Kubo, Masataka Itoh, Takahito |
| description | Asymmetric anionic polymerizations of a prochiral monomer, 7-cyano-7-phenyl-1,4-benzoquinone methide (
3
), using chiral initiators were performed under various conditions, and optically active polymers having configurational chirality in the main chain were obtained though their specific rotation values are quite small. The optically active polymer with a negative specific rotation value of −4.4° was obtained by polymerization of
3
with a lithium isopropylphenoxide (
i
PrPhOLi)/(−)-sparteine ((−)-Sp) in a mixture solution of dichloromethane/toluene ratio of 30/70 (in vol%) at −40 °C. Stereostructures of 1-mer, 2-mer, and oligomers obtained by asymmetric anionic oligomerization of
3
with
i
PrPhOLi/(−)-Sp were examined in detail. It was found that the stereoselectivity turned out to be the opposite between the initiation reaction and the propagation one. |
| doi_str_mv | 10.1007/s00289-011-0653-2 |
| format | Article |
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3
), using chiral initiators were performed under various conditions, and optically active polymers having configurational chirality in the main chain were obtained though their specific rotation values are quite small. The optically active polymer with a negative specific rotation value of −4.4° was obtained by polymerization of
3
with a lithium isopropylphenoxide (
i
PrPhOLi)/(−)-sparteine ((−)-Sp) in a mixture solution of dichloromethane/toluene ratio of 30/70 (in vol%) at −40 °C. Stereostructures of 1-mer, 2-mer, and oligomers obtained by asymmetric anionic oligomerization of
3
with
i
PrPhOLi/(−)-Sp were examined in detail. It was found that the stereoselectivity turned out to be the opposite between the initiation reaction and the propagation one.</description><identifier>ISSN: 0170-0839</identifier><identifier>EISSN: 1436-2449</identifier><identifier>DOI: 10.1007/s00289-011-0653-2</identifier><identifier>CODEN: POBUDR</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Anionic polymerization ; Applied sciences ; Asymmetry ; Benzoquinone ; Carbon ; Characterization and Evaluation of Materials ; Chemistry ; Chemistry and Materials Science ; Chirality ; Chromatography ; Complex Fluids and Microfluidics ; Dichloromethane ; Exact sciences and technology ; Ligands ; Lithium ; Oligomerization ; Optical activity ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Physicochemistry of polymers ; Polymer industry, paints, wood ; Polymer Sciences ; Polymerization ; Polymers ; Rotation ; Sensors ; Soft and Granular Matter ; Solvents ; Stereoselectivity ; Technology of polymers ; Toluene</subject><ispartof>Polymer bulletin (Berlin, Germany), 2012-04, Vol.68 (7), p.1831-1844</ispartof><rights>Springer-Verlag 2011</rights><rights>2014 INIST-CNRS</rights><rights>Springer-Verlag 2011.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-fd12a341a9c4d9c214f004a1da9da7dac5a12ab9bb93babcae852ead8cf628773</citedby><cites>FETCH-LOGICAL-c412t-fd12a341a9c4d9c214f004a1da9da7dac5a12ab9bb93babcae852ead8cf628773</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00289-011-0653-2$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2917873038?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,776,780,21368,27903,27904,33723,41467,42536,43784,51297,64361,64365,72215</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25665434$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakagawa, Risa</creatorcontrib><creatorcontrib>Uno, Takahiro</creatorcontrib><creatorcontrib>Kubo, Masataka</creatorcontrib><creatorcontrib>Itoh, Takahito</creatorcontrib><title>Asymmetric anionic polymerization of 7-cyano-7-phenyl-1,4-benzoquinone methide</title><title>Polymer bulletin (Berlin, Germany)</title><addtitle>Polym. Bull</addtitle><description>Asymmetric anionic polymerizations of a prochiral monomer, 7-cyano-7-phenyl-1,4-benzoquinone methide (
3
), using chiral initiators were performed under various conditions, and optically active polymers having configurational chirality in the main chain were obtained though their specific rotation values are quite small. The optically active polymer with a negative specific rotation value of −4.4° was obtained by polymerization of
3
with a lithium isopropylphenoxide (
i
PrPhOLi)/(−)-sparteine ((−)-Sp) in a mixture solution of dichloromethane/toluene ratio of 30/70 (in vol%) at −40 °C. Stereostructures of 1-mer, 2-mer, and oligomers obtained by asymmetric anionic oligomerization of
3
with
i
PrPhOLi/(−)-Sp were examined in detail. It was found that the stereoselectivity turned out to be the opposite between the initiation reaction and the propagation one.</description><subject>Anionic polymerization</subject><subject>Applied sciences</subject><subject>Asymmetry</subject><subject>Benzoquinone</subject><subject>Carbon</subject><subject>Characterization and Evaluation of Materials</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chirality</subject><subject>Chromatography</subject><subject>Complex Fluids and Microfluidics</subject><subject>Dichloromethane</subject><subject>Exact sciences and technology</subject><subject>Ligands</subject><subject>Lithium</subject><subject>Oligomerization</subject><subject>Optical activity</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Physicochemistry of polymers</subject><subject>Polymer industry, paints, wood</subject><subject>Polymer Sciences</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Rotation</subject><subject>Sensors</subject><subject>Soft and Granular Matter</subject><subject>Solvents</subject><subject>Stereoselectivity</subject><subject>Technology of polymers</subject><subject>Toluene</subject><issn>0170-0839</issn><issn>1436-2449</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp1kMtOwzAQRS0EEqXwAewiIXYY_EocL6uKl1TBBtbWxHFoqsQudrpIvx5XqWDFajQzZ-5cXYSuKbmnhMiHSAgrFSaUYlLkHLMTNKOCF5gJoU7RjFBJMCm5OkcXMW5I6ouCztDbIo59b4fQmgxc612qW9-NvQ3tHoY0yHyTSWxGcB5LvF1bN3aY3glcWbf337vWeWezJLFua3uJzhroor061jn6fHr8WL7g1fvz63KxwkZQNuCmpgy4oKCMqJVhVDSECKA1qBpkDSaHBFSqqhSvoDJgy5xZqEvTFKyUks_RzaS7DcmCjYPe-F1w6aVmispScsLLRNGJMsHHGGyjt6HtIYyaEn2ITU-x6RSbPsSmWbq5PSpDNNA1AZxp4-8hy4siF1wkjk1cTCv3ZcOfg__FfwBOR31e</recordid><startdate>20120401</startdate><enddate>20120401</enddate><creator>Nakagawa, Risa</creator><creator>Uno, Takahiro</creator><creator>Kubo, Masataka</creator><creator>Itoh, Takahito</creator><general>Springer-Verlag</general><general>Springer</general><general>Springer Nature B.V</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope></search><sort><creationdate>20120401</creationdate><title>Asymmetric anionic polymerization of 7-cyano-7-phenyl-1,4-benzoquinone methide</title><author>Nakagawa, Risa ; Uno, Takahiro ; Kubo, Masataka ; Itoh, Takahito</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-fd12a341a9c4d9c214f004a1da9da7dac5a12ab9bb93babcae852ead8cf628773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anionic polymerization</topic><topic>Applied sciences</topic><topic>Asymmetry</topic><topic>Benzoquinone</topic><topic>Carbon</topic><topic>Characterization and Evaluation of Materials</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chirality</topic><topic>Chromatography</topic><topic>Complex Fluids and Microfluidics</topic><topic>Dichloromethane</topic><topic>Exact sciences and technology</topic><topic>Ligands</topic><topic>Lithium</topic><topic>Oligomerization</topic><topic>Optical activity</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Physicochemistry of polymers</topic><topic>Polymer industry, paints, wood</topic><topic>Polymer Sciences</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Rotation</topic><topic>Sensors</topic><topic>Soft and Granular Matter</topic><topic>Solvents</topic><topic>Stereoselectivity</topic><topic>Technology of polymers</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nakagawa, Risa</creatorcontrib><creatorcontrib>Uno, Takahiro</creatorcontrib><creatorcontrib>Kubo, Masataka</creatorcontrib><creatorcontrib>Itoh, Takahito</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection (ProQuest)</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><jtitle>Polymer bulletin (Berlin, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakagawa, Risa</au><au>Uno, Takahiro</au><au>Kubo, Masataka</au><au>Itoh, Takahito</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric anionic polymerization of 7-cyano-7-phenyl-1,4-benzoquinone methide</atitle><jtitle>Polymer bulletin (Berlin, Germany)</jtitle><stitle>Polym. Bull</stitle><date>2012-04-01</date><risdate>2012</risdate><volume>68</volume><issue>7</issue><spage>1831</spage><epage>1844</epage><pages>1831-1844</pages><issn>0170-0839</issn><eissn>1436-2449</eissn><coden>POBUDR</coden><abstract>Asymmetric anionic polymerizations of a prochiral monomer, 7-cyano-7-phenyl-1,4-benzoquinone methide (
3
), using chiral initiators were performed under various conditions, and optically active polymers having configurational chirality in the main chain were obtained though their specific rotation values are quite small. The optically active polymer with a negative specific rotation value of −4.4° was obtained by polymerization of
3
with a lithium isopropylphenoxide (
i
PrPhOLi)/(−)-sparteine ((−)-Sp) in a mixture solution of dichloromethane/toluene ratio of 30/70 (in vol%) at −40 °C. Stereostructures of 1-mer, 2-mer, and oligomers obtained by asymmetric anionic oligomerization of
3
with
i
PrPhOLi/(−)-Sp were examined in detail. It was found that the stereoselectivity turned out to be the opposite between the initiation reaction and the propagation one.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><doi>10.1007/s00289-011-0653-2</doi><tpages>14</tpages></addata></record> |
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| subjects | Anionic polymerization Applied sciences Asymmetry Benzoquinone Carbon Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Chirality Chromatography Complex Fluids and Microfluidics Dichloromethane Exact sciences and technology Ligands Lithium Oligomerization Optical activity Organic Chemistry Original Paper Physical Chemistry Physicochemistry of polymers Polymer industry, paints, wood Polymer Sciences Polymerization Polymers Rotation Sensors Soft and Granular Matter Solvents Stereoselectivity Technology of polymers Toluene |
| title | Asymmetric anionic polymerization of 7-cyano-7-phenyl-1,4-benzoquinone methide |
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