Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety

A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme)....

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2013-01, Vol.52 (5), p.1560-1563
Hauptverfasser: Yanai, Hikaru, Yoshino, Tasuku, Fujita, Masaya, Fukaya, Haruhiko, Kotani, Akira, Kusu, Fumiyo, Taguchi, Takeo
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1563
container_issue 5
container_start_page 1560
container_title Angewandte Chemie International Edition
container_volume 52
creator Yanai, Hikaru
Yoshino, Tasuku
Fujita, Masaya
Fukaya, Haruhiko
Kotani, Akira
Kusu, Fumiyo
Taguchi, Takeo
description A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).
doi_str_mv 10.1002/anie.201208809
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1701043888</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2872083111</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5479-eb65e4dd88593d593443c811b563f06895e0db261169443a26e329fbe96dc7ef3</originalsourceid><addsrcrecordid>eNqF0c1PFDEYB-DGaATRq0cziRcPzNqP6ddxM0EgLGtEjAmXpjPzjhRn26WdDS5_PV0XNsYLh6Zfz_tLmxeh9wRPCMb0s_UOJhQTipXC-gXaJ5ySkknJXuZ1xVgpFSd76E1KN9lnJF6jPcoo07yq9tHV97UfryG5dFjU1zbadoTo7u3ogj8srO-K6XI5uPbvQSpCX1zduXFjNts6-NE67_yvwha1jU1-TvDFeXAwrt-iV70dErx7nA_Qjy9Hl_VJOft6fFpPZ2XLK6lLaASHquuU4pp1eVQVaxUhDResx0JpDrhrqCBE6HxlqQBGdd-AFl0roWcH6NM2dxnD7QrSaBYutTAM1kNYJUMkJrhiSqnnKVUUV4RjkenH_-hNWEWfP5KVpJhrQnVWk61qY0gpQm-W0S1sXBuCzaZBZtMgs2tQLvjwGLtqFtDt-FNHMtBbcOcGWD8TZ6bz06N_w8ttrUsj_NnV2vjbCMkkNz_nx2b-7WJ2WZ9pc8EeADBzqp0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1272059129</pqid></control><display><type>article</type><title>Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety</title><source>MEDLINE</source><source>Wiley Online Library All Journals</source><creator>Yanai, Hikaru ; Yoshino, Tasuku ; Fujita, Masaya ; Fukaya, Haruhiko ; Kotani, Akira ; Kusu, Fumiyo ; Taguchi, Takeo</creator><creatorcontrib>Yanai, Hikaru ; Yoshino, Tasuku ; Fujita, Masaya ; Fukaya, Haruhiko ; Kotani, Akira ; Kusu, Fumiyo ; Taguchi, Takeo</creatorcontrib><description>A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201208809</identifier><identifier>PMID: 23239544</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>aldol reaction ; Aniline ; Anions - chemistry ; carbanions ; Carbon - chemistry ; Catalysts ; Crystallography, X-Ray ; homogeneous catalysis ; Molecular Conformation ; Quaternary Ammonium Compounds - chemistry ; Rings (mathematics) ; Synthesis ; synthetic methodology ; zwitterions</subject><ispartof>Angewandte Chemie International Edition, 2013-01, Vol.52 (5), p.1560-1563</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5479-eb65e4dd88593d593443c811b563f06895e0db261169443a26e329fbe96dc7ef3</citedby><cites>FETCH-LOGICAL-c5479-eb65e4dd88593d593443c811b563f06895e0db261169443a26e329fbe96dc7ef3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201208809$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201208809$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23239544$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yanai, Hikaru</creatorcontrib><creatorcontrib>Yoshino, Tasuku</creatorcontrib><creatorcontrib>Fujita, Masaya</creatorcontrib><creatorcontrib>Fukaya, Haruhiko</creatorcontrib><creatorcontrib>Kotani, Akira</creatorcontrib><creatorcontrib>Kusu, Fumiyo</creatorcontrib><creatorcontrib>Taguchi, Takeo</creatorcontrib><title>Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).</description><subject>aldol reaction</subject><subject>Aniline</subject><subject>Anions - chemistry</subject><subject>carbanions</subject><subject>Carbon - chemistry</subject><subject>Catalysts</subject><subject>Crystallography, X-Ray</subject><subject>homogeneous catalysis</subject><subject>Molecular Conformation</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Rings (mathematics)</subject><subject>Synthesis</subject><subject>synthetic methodology</subject><subject>zwitterions</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1PFDEYB-DGaATRq0cziRcPzNqP6ddxM0EgLGtEjAmXpjPzjhRn26WdDS5_PV0XNsYLh6Zfz_tLmxeh9wRPCMb0s_UOJhQTipXC-gXaJ5ySkknJXuZ1xVgpFSd76E1KN9lnJF6jPcoo07yq9tHV97UfryG5dFjU1zbadoTo7u3ogj8srO-K6XI5uPbvQSpCX1zduXFjNts6-NE67_yvwha1jU1-TvDFeXAwrt-iV70dErx7nA_Qjy9Hl_VJOft6fFpPZ2XLK6lLaASHquuU4pp1eVQVaxUhDResx0JpDrhrqCBE6HxlqQBGdd-AFl0roWcH6NM2dxnD7QrSaBYutTAM1kNYJUMkJrhiSqnnKVUUV4RjkenH_-hNWEWfP5KVpJhrQnVWk61qY0gpQm-W0S1sXBuCzaZBZtMgs2tQLvjwGLtqFtDt-FNHMtBbcOcGWD8TZ6bz06N_w8ttrUsj_NnV2vjbCMkkNz_nx2b-7WJ2WZ9pc8EeADBzqp0</recordid><startdate>20130128</startdate><enddate>20130128</enddate><creator>Yanai, Hikaru</creator><creator>Yoshino, Tasuku</creator><creator>Fujita, Masaya</creator><creator>Fukaya, Haruhiko</creator><creator>Kotani, Akira</creator><creator>Kusu, Fumiyo</creator><creator>Taguchi, Takeo</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20130128</creationdate><title>Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety</title><author>Yanai, Hikaru ; Yoshino, Tasuku ; Fujita, Masaya ; Fukaya, Haruhiko ; Kotani, Akira ; Kusu, Fumiyo ; Taguchi, Takeo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5479-eb65e4dd88593d593443c811b563f06895e0db261169443a26e329fbe96dc7ef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>aldol reaction</topic><topic>Aniline</topic><topic>Anions - chemistry</topic><topic>carbanions</topic><topic>Carbon - chemistry</topic><topic>Catalysts</topic><topic>Crystallography, X-Ray</topic><topic>homogeneous catalysis</topic><topic>Molecular Conformation</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Rings (mathematics)</topic><topic>Synthesis</topic><topic>synthetic methodology</topic><topic>zwitterions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yanai, Hikaru</creatorcontrib><creatorcontrib>Yoshino, Tasuku</creatorcontrib><creatorcontrib>Fujita, Masaya</creatorcontrib><creatorcontrib>Fukaya, Haruhiko</creatorcontrib><creatorcontrib>Kotani, Akira</creatorcontrib><creatorcontrib>Kusu, Fumiyo</creatorcontrib><creatorcontrib>Taguchi, Takeo</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yanai, Hikaru</au><au>Yoshino, Tasuku</au><au>Fujita, Masaya</au><au>Fukaya, Haruhiko</au><au>Kotani, Akira</au><au>Kusu, Fumiyo</au><au>Taguchi, Takeo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2013-01-28</date><risdate>2013</risdate><volume>52</volume><issue>5</issue><spage>1560</spage><epage>1563</epage><pages>1560-1563</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23239544</pmid><doi>10.1002/anie.201208809</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2013-01, Vol.52 (5), p.1560-1563
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_1701043888
source MEDLINE; Wiley Online Library All Journals
subjects aldol reaction
Aniline
Anions - chemistry
carbanions
Carbon - chemistry
Catalysts
Crystallography, X-Ray
homogeneous catalysis
Molecular Conformation
Quaternary Ammonium Compounds - chemistry
Rings (mathematics)
Synthesis
synthetic methodology
zwitterions
title Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T08%3A09%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis,%20Characterization,%20and%20Applications%20of%20Zwitterions%20Containing%20a%20Carbanion%20Moiety&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Yanai,%20Hikaru&rft.date=2013-01-28&rft.volume=52&rft.issue=5&rft.spage=1560&rft.epage=1563&rft.pages=1560-1563&rft.issn=1433-7851&rft.eissn=1521-3773&rft.coden=ACIEAY&rft_id=info:doi/10.1002/anie.201208809&rft_dat=%3Cproquest_cross%3E2872083111%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1272059129&rft_id=info:pmid/23239544&rfr_iscdi=true