Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution
Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, t...
Gespeichert in:
| Veröffentlicht in: | Journal of physical organic chemistry 2013-08, Vol.26 (8), p.675-678 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 678 |
|---|---|
| container_issue | 8 |
| container_start_page | 675 |
| container_title | Journal of physical organic chemistry |
| container_volume | 26 |
| creator | Salin, Alexey V. Fatkhutdinov, Albert R. Il'in, Anton V. Sotov, Evgeniy I. Sobanov, Alexandr A. Galkin, Vladimir I. James, Brian R. |
| description | Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. Copyright © 2013 John Wiley & Sons, Ltd.
Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. |
| doi_str_mv | 10.1002/poc.3154 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1400018088</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3019818861</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3644-8bbb8fbb146290a00f64a839d1d4fe2ea64ec5066e762662afc02aab69ca3b4a3</originalsourceid><addsrcrecordid>eNp10EFLwzAUB_AgCs4p-BECXrx0Jk2atkcZuglzU1D0FtL0lWarSU065r693SaCB0_hkR__x_sjdEnJiBIS37ROjxhN-BEaUJLnEWV5cowGJMt5xGJGTtFZCEtC-r8kHSD7CLpW1oTOaKxCC7oL2FXYg9KdcXY_dN60Ndht09YutLWxgDemqzE0PffORiVURhuwHVbNCiwEbCxWGvah2pQ4uGa9iztHJ5VqAlz8vEP0en_3Mp5Gs8XkYXw7izQTnEdZURRZVRSUizgnipBKcJWxvKQlryAGJTjohAgBqYiFiFWlSaxUIXKtWMEVG6KrQ27r3ecaQieXbu1tv1JS3h9PM5Jlvbo-KO1dCB4q2XrzofxWUiJ3bcq-Tblrs6fRgW5MA9t_nXxajP_6vln4-vXKr6RIWZrIt_lETp_H83dOM5mwbw3th10</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1400018088</pqid></control><display><type>article</type><title>Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Salin, Alexey V. ; Fatkhutdinov, Albert R. ; Il'in, Anton V. ; Sotov, Evgeniy I. ; Sobanov, Alexandr A. ; Galkin, Vladimir I. ; James, Brian R.</creator><creatorcontrib>Salin, Alexey V. ; Fatkhutdinov, Albert R. ; Il'in, Anton V. ; Sotov, Evgeniy I. ; Sobanov, Alexandr A. ; Galkin, Vladimir I. ; James, Brian R.</creatorcontrib><description>Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. Copyright © 2013 John Wiley & Sons, Ltd.
Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid.</description><identifier>ISSN: 0894-3230</identifier><identifier>EISSN: 1099-1395</identifier><identifier>DOI: 10.1002/poc.3154</identifier><language>eng</language><publisher>Bognor Regis: Blackwell Publishing Ltd</publisher><subject>phosphonium zwitterions ; proton transfer ; rate-determining step ; reaction mechanism ; solvent isotope effect</subject><ispartof>Journal of physical organic chemistry, 2013-08, Vol.26 (8), p.675-678</ispartof><rights>Copyright © 2013 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3644-8bbb8fbb146290a00f64a839d1d4fe2ea64ec5066e762662afc02aab69ca3b4a3</citedby><cites>FETCH-LOGICAL-c3644-8bbb8fbb146290a00f64a839d1d4fe2ea64ec5066e762662afc02aab69ca3b4a3</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%2Fpoc.3154$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpoc.3154$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Salin, Alexey V.</creatorcontrib><creatorcontrib>Fatkhutdinov, Albert R.</creatorcontrib><creatorcontrib>Il'in, Anton V.</creatorcontrib><creatorcontrib>Sotov, Evgeniy I.</creatorcontrib><creatorcontrib>Sobanov, Alexandr A.</creatorcontrib><creatorcontrib>Galkin, Vladimir I.</creatorcontrib><creatorcontrib>James, Brian R.</creatorcontrib><title>Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution</title><title>Journal of physical organic chemistry</title><addtitle>J. Phys. Org. Chem</addtitle><description>Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. Copyright © 2013 John Wiley & Sons, Ltd.
Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid.</description><subject>phosphonium zwitterions</subject><subject>proton transfer</subject><subject>rate-determining step</subject><subject>reaction mechanism</subject><subject>solvent isotope effect</subject><issn>0894-3230</issn><issn>1099-1395</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp10EFLwzAUB_AgCs4p-BECXrx0Jk2atkcZuglzU1D0FtL0lWarSU065r693SaCB0_hkR__x_sjdEnJiBIS37ROjxhN-BEaUJLnEWV5cowGJMt5xGJGTtFZCEtC-r8kHSD7CLpW1oTOaKxCC7oL2FXYg9KdcXY_dN60Ndht09YutLWxgDemqzE0PffORiVURhuwHVbNCiwEbCxWGvah2pQ4uGa9iztHJ5VqAlz8vEP0en_3Mp5Gs8XkYXw7izQTnEdZURRZVRSUizgnipBKcJWxvKQlryAGJTjohAgBqYiFiFWlSaxUIXKtWMEVG6KrQ27r3ecaQieXbu1tv1JS3h9PM5Jlvbo-KO1dCB4q2XrzofxWUiJ3bcq-Tblrs6fRgW5MA9t_nXxajP_6vln4-vXKr6RIWZrIt_lETp_H83dOM5mwbw3th10</recordid><startdate>201308</startdate><enddate>201308</enddate><creator>Salin, Alexey V.</creator><creator>Fatkhutdinov, Albert R.</creator><creator>Il'in, Anton V.</creator><creator>Sotov, Evgeniy I.</creator><creator>Sobanov, Alexandr A.</creator><creator>Galkin, Vladimir I.</creator><creator>James, Brian R.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201308</creationdate><title>Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution</title><author>Salin, Alexey V. ; Fatkhutdinov, Albert R. ; Il'in, Anton V. ; Sotov, Evgeniy I. ; Sobanov, Alexandr A. ; Galkin, Vladimir I. ; James, Brian R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3644-8bbb8fbb146290a00f64a839d1d4fe2ea64ec5066e762662afc02aab69ca3b4a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>phosphonium zwitterions</topic><topic>proton transfer</topic><topic>rate-determining step</topic><topic>reaction mechanism</topic><topic>solvent isotope effect</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Salin, Alexey V.</creatorcontrib><creatorcontrib>Fatkhutdinov, Albert R.</creatorcontrib><creatorcontrib>Il'in, Anton V.</creatorcontrib><creatorcontrib>Sotov, Evgeniy I.</creatorcontrib><creatorcontrib>Sobanov, Alexandr A.</creatorcontrib><creatorcontrib>Galkin, Vladimir I.</creatorcontrib><creatorcontrib>James, Brian R.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Journal of physical organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Salin, Alexey V.</au><au>Fatkhutdinov, Albert R.</au><au>Il'in, Anton V.</au><au>Sotov, Evgeniy I.</au><au>Sobanov, Alexandr A.</au><au>Galkin, Vladimir I.</au><au>James, Brian R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution</atitle><jtitle>Journal of physical organic chemistry</jtitle><addtitle>J. Phys. Org. Chem</addtitle><date>2013-08</date><risdate>2013</risdate><volume>26</volume><issue>8</issue><spage>675</spage><epage>678</epage><pages>675-678</pages><issn>0894-3230</issn><eissn>1099-1395</eissn><abstract>Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. Copyright © 2013 John Wiley & Sons, Ltd.
Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid.</abstract><cop>Bognor Regis</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/poc.3154</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0894-3230 |
| ispartof | Journal of physical organic chemistry, 2013-08, Vol.26 (8), p.675-678 |
| issn | 0894-3230 1099-1395 |
| language | eng |
| recordid | cdi_proquest_journals_1400018088 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | phosphonium zwitterions proton transfer rate-determining step reaction mechanism solvent isotope effect |
| title | Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T14%3A09%3A14IST&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=Mechanistic%20aspects%20of%20reactions%20of%20triphenylphosphine%20with%20electron-deficient%20alkenes%20in%20acetic%20acid%20solution&rft.jtitle=Journal%20of%20physical%20organic%20chemistry&rft.au=Salin,%20Alexey%20V.&rft.date=2013-08&rft.volume=26&rft.issue=8&rft.spage=675&rft.epage=678&rft.pages=675-678&rft.issn=0894-3230&rft.eissn=1099-1395&rft_id=info:doi/10.1002/poc.3154&rft_dat=%3Cproquest_cross%3E3019818861%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=1400018088&rft_id=info:pmid/&rfr_iscdi=true |