Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory
This paper describes the design and implementation of a minimally hazardous, environmentally friendly, and energy efficient sequential reaction sequence within a sophomore level Organic Chemistry lab course to efficiently synthesize N-phenylmaleimide precursors for a Diels-Alder reaction. Substitute...
Gespeichert in:
| Veröffentlicht in: | Green chemistry letters and reviews 2019-04, Vol.12 (2), p.127-135 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 135 |
|---|---|
| container_issue | 2 |
| container_start_page | 127 |
| container_title | Green chemistry letters and reviews |
| container_volume | 12 |
| creator | Bastin, Loyd D. Nigam, Manisha Martinus, Sam Maloney, James E. Benyack, Landon L. Gainer, Brendan |
| description | This paper describes the design and implementation of a minimally hazardous, environmentally friendly, and energy efficient sequential reaction sequence within a sophomore level Organic Chemistry lab course to efficiently synthesize N-phenylmaleimide precursors for a Diels-Alder reaction. Substituted N-phenylmaleimides are a class of very expensive precursors of considerable interest due to their biological properties and use as intermediates in synthesis. The synthesis described herein produces a substituted N-phenylmaleimide in two steps from maleic anhydride and a substituted aniline followed by its Diels-Alder reaction with 2,5-dimethylfuran. The experiment exposes students to the green chemistry principles of atom economy, use of safer chemicals, design for energy efficiency, waste reduction, and inherently safer chemistry for accident prevention and enables students to use
1
H NMR spectroscopy to characterize the products. |
| doi_str_mv | 10.1080/17518253.2019.1609596 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_proquest_journals_2316428584</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_debaa45197434cf6b6c0169374e42cf0</doaj_id><sourcerecordid>2316428584</sourcerecordid><originalsourceid>FETCH-LOGICAL-c451t-ba39c8d346f6bf982fb1ed966758815a3bd2a01545b268cdd8d1f5bef5d0da8f3</originalsourceid><addsrcrecordid>eNp9kcFu1DAURSMEEqXwCUiWWGewk9hxWFEVaCtVsADW1ov9POORYw-2oyo_g_gWvowMM3TJytbTvec-vVtVrxndMCrpW9ZzJhvebhrKhg0TdOCDeFJdHOd1z4bm6fl_FD2vXuS8p1RQ3nQX1c-vSyg7zC6TaEmex1xcmQsa8rk-7DAsfgKPbnIGM4FgyJyRuECAfHDoc33lDSaSEHRxMbwj8PvXNiEGMs2-uDoXPJD8GGFjWiFkDqtpm8DMUJDEtIXgNNE7nFwuaSEexpigxLS8rJ5Z8Blfnd_L6vunj9-ub-v7Lzd311f3te44K_UI7aClaTthxWgH2diRoRmE6LmUjEM7mgYo4x0fGyG1MdIwy0e03FAD0raX1d2JayLs1SG5CdKiIjj1d7CuqCAVpz0qgyPAmjr0XdvpNU9oysTQ9h12jbZ0Zb05sQ4p_pgxF7WPcwrr-qppmegayWW3qvhJpVPMOaF9TGVUHWtV_2pVx1rVudbV9_7kc2G95gQPMXmjCiw-JpsgaJdV-3_EH_mpriE</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2316428584</pqid></control><display><type>article</type><title>Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory</title><source>Taylor & Francis Open Access</source><source>DOAJ Directory of Open Access Journals</source><source>Free E-Journal (出版社公開部分のみ）</source><source>Free Full-Text Journals in Chemistry</source><creator>Bastin, Loyd D. ; Nigam, Manisha ; Martinus, Sam ; Maloney, James E. ; Benyack, Landon L. ; Gainer, Brendan</creator><creatorcontrib>Bastin, Loyd D. ; Nigam, Manisha ; Martinus, Sam ; Maloney, James E. ; Benyack, Landon L. ; Gainer, Brendan</creatorcontrib><description>This paper describes the design and implementation of a minimally hazardous, environmentally friendly, and energy efficient sequential reaction sequence within a sophomore level Organic Chemistry lab course to efficiently synthesize N-phenylmaleimide precursors for a Diels-Alder reaction. Substituted N-phenylmaleimides are a class of very expensive precursors of considerable interest due to their biological properties and use as intermediates in synthesis. The synthesis described herein produces a substituted N-phenylmaleimide in two steps from maleic anhydride and a substituted aniline followed by its Diels-Alder reaction with 2,5-dimethylfuran. The experiment exposes students to the green chemistry principles of atom economy, use of safer chemicals, design for energy efficiency, waste reduction, and inherently safer chemistry for accident prevention and enables students to use
1
H NMR spectroscopy to characterize the products.</description><identifier>ISSN: 1751-8253</identifier><identifier>EISSN: 1751-7192</identifier><identifier>DOI: 10.1080/17518253.2019.1609596</identifier><language>eng</language><publisher>Abingdon: Taylor & Francis</publisher><subject>Accident prevention ; amine acylation ; Aniline ; Atom economy ; Biological properties ; Chemical synthesis ; Diels-Alder ; Energy efficiency ; Forensic engineering ; Green chemistry ; Intermediates ; Magnetic resonance spectroscopy ; Maleic anhydride ; maleimide ; multi-step synthesis ; NMR ; NMR spectroscopy ; Nuclear magnetic resonance ; Organic chemistry ; Precursors ; Students ; Substitutes ; Undergraduate organic chemistry</subject><ispartof>Green chemistry letters and reviews, 2019-04, Vol.12 (2), p.127-135</ispartof><rights>2019 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group 2019</rights><rights>2019 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. This work is licensed under the Creative Commons Attribution – Non-Commercial License http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c451t-ba39c8d346f6bf982fb1ed966758815a3bd2a01545b268cdd8d1f5bef5d0da8f3</citedby><cites>FETCH-LOGICAL-c451t-ba39c8d346f6bf982fb1ed966758815a3bd2a01545b268cdd8d1f5bef5d0da8f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/17518253.2019.1609596$$EPDF$$P50$$Ginformaworld$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/17518253.2019.1609596$$EHTML$$P50$$Ginformaworld$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,864,2102,27502,27924,27925,59143,59144</link.rule.ids></links><search><creatorcontrib>Bastin, Loyd D.</creatorcontrib><creatorcontrib>Nigam, Manisha</creatorcontrib><creatorcontrib>Martinus, Sam</creatorcontrib><creatorcontrib>Maloney, James E.</creatorcontrib><creatorcontrib>Benyack, Landon L.</creatorcontrib><creatorcontrib>Gainer, Brendan</creatorcontrib><title>Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory</title><title>Green chemistry letters and reviews</title><description>This paper describes the design and implementation of a minimally hazardous, environmentally friendly, and energy efficient sequential reaction sequence within a sophomore level Organic Chemistry lab course to efficiently synthesize N-phenylmaleimide precursors for a Diels-Alder reaction. Substituted N-phenylmaleimides are a class of very expensive precursors of considerable interest due to their biological properties and use as intermediates in synthesis. The synthesis described herein produces a substituted N-phenylmaleimide in two steps from maleic anhydride and a substituted aniline followed by its Diels-Alder reaction with 2,5-dimethylfuran. The experiment exposes students to the green chemistry principles of atom economy, use of safer chemicals, design for energy efficiency, waste reduction, and inherently safer chemistry for accident prevention and enables students to use
1
H NMR spectroscopy to characterize the products.</description><subject>Accident prevention</subject><subject>amine acylation</subject><subject>Aniline</subject><subject>Atom economy</subject><subject>Biological properties</subject><subject>Chemical synthesis</subject><subject>Diels-Alder</subject><subject>Energy efficiency</subject><subject>Forensic engineering</subject><subject>Green chemistry</subject><subject>Intermediates</subject><subject>Magnetic resonance spectroscopy</subject><subject>Maleic anhydride</subject><subject>maleimide</subject><subject>multi-step synthesis</subject><subject>NMR</subject><subject>NMR spectroscopy</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Precursors</subject><subject>Students</subject><subject>Substitutes</subject><subject>Undergraduate organic chemistry</subject><issn>1751-8253</issn><issn>1751-7192</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>0YH</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>DOA</sourceid><recordid>eNp9kcFu1DAURSMEEqXwCUiWWGewk9hxWFEVaCtVsADW1ov9POORYw-2oyo_g_gWvowMM3TJytbTvec-vVtVrxndMCrpW9ZzJhvebhrKhg0TdOCDeFJdHOd1z4bm6fl_FD2vXuS8p1RQ3nQX1c-vSyg7zC6TaEmex1xcmQsa8rk-7DAsfgKPbnIGM4FgyJyRuECAfHDoc33lDSaSEHRxMbwj8PvXNiEGMs2-uDoXPJD8GGFjWiFkDqtpm8DMUJDEtIXgNNE7nFwuaSEexpigxLS8rJ5Z8Blfnd_L6vunj9-ub-v7Lzd311f3te44K_UI7aClaTthxWgH2diRoRmE6LmUjEM7mgYo4x0fGyG1MdIwy0e03FAD0raX1d2JayLs1SG5CdKiIjj1d7CuqCAVpz0qgyPAmjr0XdvpNU9oysTQ9h12jbZ0Zb05sQ4p_pgxF7WPcwrr-qppmegayWW3qvhJpVPMOaF9TGVUHWtV_2pVx1rVudbV9_7kc2G95gQPMXmjCiw-JpsgaJdV-3_EH_mpriE</recordid><startdate>20190403</startdate><enddate>20190403</enddate><creator>Bastin, Loyd D.</creator><creator>Nigam, Manisha</creator><creator>Martinus, Sam</creator><creator>Maloney, James E.</creator><creator>Benyack, Landon L.</creator><creator>Gainer, Brendan</creator><general>Taylor & Francis</general><general>Taylor & Francis Ltd</general><general>Taylor & Francis Group</general><scope>0YH</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>L6V</scope><scope>M7S</scope><scope>PATMY</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>DOA</scope></search><sort><creationdate>20190403</creationdate><title>Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory</title><author>Bastin, Loyd D. ; Nigam, Manisha ; Martinus, Sam ; Maloney, James E. ; Benyack, Landon L. ; Gainer, Brendan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c451t-ba39c8d346f6bf982fb1ed966758815a3bd2a01545b268cdd8d1f5bef5d0da8f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Accident prevention</topic><topic>amine acylation</topic><topic>Aniline</topic><topic>Atom economy</topic><topic>Biological properties</topic><topic>Chemical synthesis</topic><topic>Diels-Alder</topic><topic>Energy efficiency</topic><topic>Forensic engineering</topic><topic>Green chemistry</topic><topic>Intermediates</topic><topic>Magnetic resonance spectroscopy</topic><topic>Maleic anhydride</topic><topic>maleimide</topic><topic>multi-step synthesis</topic><topic>NMR</topic><topic>NMR spectroscopy</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Precursors</topic><topic>Students</topic><topic>Substitutes</topic><topic>Undergraduate organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bastin, Loyd D.</creatorcontrib><creatorcontrib>Nigam, Manisha</creatorcontrib><creatorcontrib>Martinus, Sam</creatorcontrib><creatorcontrib>Maloney, James E.</creatorcontrib><creatorcontrib>Benyack, Landon L.</creatorcontrib><creatorcontrib>Gainer, Brendan</creatorcontrib><collection>Taylor & Francis Open Access</collection><collection>CrossRef</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>ProQuest Engineering Collection</collection><collection>Engineering Database</collection><collection>Environmental Science Database</collection><collection>Materials science collection</collection><collection>Publicly Available Content (ProQuest)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Engineering collection</collection><collection>Environmental Science Collection</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Green chemistry letters and reviews</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bastin, Loyd D.</au><au>Nigam, Manisha</au><au>Martinus, Sam</au><au>Maloney, James E.</au><au>Benyack, Landon L.</au><au>Gainer, Brendan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory</atitle><jtitle>Green chemistry letters and reviews</jtitle><date>2019-04-03</date><risdate>2019</risdate><volume>12</volume><issue>2</issue><spage>127</spage><epage>135</epage><pages>127-135</pages><issn>1751-8253</issn><eissn>1751-7192</eissn><abstract>This paper describes the design and implementation of a minimally hazardous, environmentally friendly, and energy efficient sequential reaction sequence within a sophomore level Organic Chemistry lab course to efficiently synthesize N-phenylmaleimide precursors for a Diels-Alder reaction. Substituted N-phenylmaleimides are a class of very expensive precursors of considerable interest due to their biological properties and use as intermediates in synthesis. The synthesis described herein produces a substituted N-phenylmaleimide in two steps from maleic anhydride and a substituted aniline followed by its Diels-Alder reaction with 2,5-dimethylfuran. The experiment exposes students to the green chemistry principles of atom economy, use of safer chemicals, design for energy efficiency, waste reduction, and inherently safer chemistry for accident prevention and enables students to use
1
H NMR spectroscopy to characterize the products.</abstract><cop>Abingdon</cop><pub>Taylor & Francis</pub><doi>10.1080/17518253.2019.1609596</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1751-8253 |
| ispartof | Green chemistry letters and reviews, 2019-04, Vol.12 (2), p.127-135 |
| issn | 1751-8253 1751-7192 |
| language | eng |
| recordid | cdi_proquest_journals_2316428584 |
| source | Taylor & Francis Open Access; DOAJ Directory of Open Access Journals; Free E-Journal (出版社公開部分のみ）; Free Full-Text Journals in Chemistry |
| subjects | Accident prevention amine acylation Aniline Atom economy Biological properties Chemical synthesis Diels-Alder Energy efficiency Forensic engineering Green chemistry Intermediates Magnetic resonance spectroscopy Maleic anhydride maleimide multi-step synthesis NMR NMR spectroscopy Nuclear magnetic resonance Organic chemistry Precursors Students Substitutes Undergraduate organic chemistry |
| title | Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T07%3A43%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20substituted%20N-phenylmaleimides%20and%20use%20in%20a%20Diels-Alder%20reaction:%20a%C2%A0green%20multi-step%20synthesis%20for%20an%20undergraduate%20organic%20chemistry%20laboratory&rft.jtitle=Green%20chemistry%20letters%20and%20reviews&rft.au=Bastin,%20Loyd%20D.&rft.date=2019-04-03&rft.volume=12&rft.issue=2&rft.spage=127&rft.epage=135&rft.pages=127-135&rft.issn=1751-8253&rft.eissn=1751-7192&rft_id=info:doi/10.1080/17518253.2019.1609596&rft_dat=%3Cproquest_doaj_%3E2316428584%3C/proquest_doaj_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2316428584&rft_id=info:pmid/&rft_doaj_id=oai_doaj_org_article_debaa45197434cf6b6c0169374e42cf0&rfr_iscdi=true |