O-SILYLATION OF SOME UNSATURATED CYCLIC PHOSPHINE OXIDES
The phosphoryl oxygen of 1.6-dihydrophosphinine oxides is silylated rapidly at room temperature by bis(trimethylsilyl)trifluoroacetamide; the product loses a ring proton to establish the resonance stabilized γ 5 -phosphinine ring system. Similar events take place with a 3-keto derivative of a tetrah...
Gespeichert in:
| Veröffentlicht in: | Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1990-09, Vol.54 (1-4), p.1-7 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7 |
|---|---|
| container_issue | 1-4 |
| container_start_page | 1 |
| container_title | Phosphorus, sulfur, and silicon and the related elements |
| container_volume | 54 |
| creator | Quin, Louis D. Kisalus, John C. Skolimowski, Janusch J. Rao, Nandakumar S. |
| description | The phosphoryl oxygen of 1.6-dihydrophosphinine oxides is silylated rapidly at room temperature by bis(trimethylsilyl)trifluoroacetamide; the product loses a ring proton to establish the resonance stabilized γ
5
-phosphinine ring system. Similar events take place with a 3-keto derivative of a tetrahydrophosphinine oxide, which also undergoes silylation of the keto oxygen. 1,4-Dihydro-lazaphosphinine are silylated to give 1,4-aza-γ
5
-phosphinines; their dibenzo derivatives (5,10-dihydrophenophosphazine oxides) require more forcing conditions (triethylsilyl bromide at 100°C) for phosphoryl silylation. These conditions are also effective for silylation of a 3-phospholene oxide. |
| doi_str_mv | 10.1080/10426509008042114 |
| format | Article |
| fullrecord | <record><control><sourceid>pascalfrancis_cross</sourceid><recordid>TN_cdi_pascalfrancis_primary_19369597</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>19369597</sourcerecordid><originalsourceid>FETCH-LOGICAL-c328t-17920e1dfd718396fdd1c9b6a8ae554f78f044d99514657bafa83896cd77e18b3</originalsourceid><addsrcrecordid>eNp1j8tKw0AUhgdRsFYfwF02LqNzMndwE9LUBmKnmBTsKkwzGaikTZkUSt_eSBUX4upc-L5z-BG6B_wIWOInwDTiDCs8DDQCoBdoBIyTkJGIXQ79sA0HQFyjm77_wBiriOARkjossnyVx2Wm54GeBoV-TYPlvIjL5VtcppMgWSV5lgSLmS4Ws2yeBvo9m6TFLbpypu2bu-86RstpWiazMNcvWRLnYU0ieQhBqAg3YJ0VIInizlqo1ZobaRrGqBPSYUqtUgwoZ2JtnJFEKl5bIRqQazJGcL5b-67vfeOqvd9sjT9VgKuv6NWf6IPzcHb2pq9N67zZ1Zv-V1SEK6bEwD2fuc3OdX5rjp1vbXUwp7bzPxL5_80n09Zk_g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>O-SILYLATION OF SOME UNSATURATED CYCLIC PHOSPHINE OXIDES</title><source>Taylor & Francis Journals Complete</source><creator>Quin, Louis D. ; Kisalus, John C. ; Skolimowski, Janusch J. ; Rao, Nandakumar S.</creator><creatorcontrib>Quin, Louis D. ; Kisalus, John C. ; Skolimowski, Janusch J. ; Rao, Nandakumar S.</creatorcontrib><description>The phosphoryl oxygen of 1.6-dihydrophosphinine oxides is silylated rapidly at room temperature by bis(trimethylsilyl)trifluoroacetamide; the product loses a ring proton to establish the resonance stabilized γ
5
-phosphinine ring system. Similar events take place with a 3-keto derivative of a tetrahydrophosphinine oxide, which also undergoes silylation of the keto oxygen. 1,4-Dihydro-lazaphosphinine are silylated to give 1,4-aza-γ
5
-phosphinines; their dibenzo derivatives (5,10-dihydrophenophosphazine oxides) require more forcing conditions (triethylsilyl bromide at 100°C) for phosphoryl silylation. These conditions are also effective for silylation of a 3-phospholene oxide.</description><identifier>ISSN: 1042-6507</identifier><identifier>EISSN: 1563-5325</identifier><identifier>DOI: 10.1080/10426509008042114</identifier><identifier>CODEN: PSSLEC</identifier><language>eng</language><publisher>Philadelphia, PA: Taylor & Francis Group</publisher><subject>1,4-dihydro-1,4-azaphosphinine-1-oxides ; 1,6-dihydrophosphinine-1-oxides ; 5,10-dihydrophenophosphazine-10-oxide ; Chemistry ; Exact sciences and technology ; Key words ; O-silyl 1,4-aza- γ ; O-silyl γ ; Organic chemistry ; Organometalloidal and organometallic compounds ; P derivatives ; phosphinines ; Preparations and properties ; trialkylsilylation</subject><ispartof>Phosphorus, sulfur, and silicon and the related elements, 1990-09, Vol.54 (1-4), p.1-7</ispartof><rights>Copyright Taylor & Francis Group, LLC 1990</rights><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c328t-17920e1dfd718396fdd1c9b6a8ae554f78f044d99514657bafa83896cd77e18b3</citedby><cites>FETCH-LOGICAL-c328t-17920e1dfd718396fdd1c9b6a8ae554f78f044d99514657bafa83896cd77e18b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/10426509008042114$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/10426509008042114$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,59646,60435</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19369597$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Quin, Louis D.</creatorcontrib><creatorcontrib>Kisalus, John C.</creatorcontrib><creatorcontrib>Skolimowski, Janusch J.</creatorcontrib><creatorcontrib>Rao, Nandakumar S.</creatorcontrib><title>O-SILYLATION OF SOME UNSATURATED CYCLIC PHOSPHINE OXIDES</title><title>Phosphorus, sulfur, and silicon and the related elements</title><description>The phosphoryl oxygen of 1.6-dihydrophosphinine oxides is silylated rapidly at room temperature by bis(trimethylsilyl)trifluoroacetamide; the product loses a ring proton to establish the resonance stabilized γ
5
-phosphinine ring system. Similar events take place with a 3-keto derivative of a tetrahydrophosphinine oxide, which also undergoes silylation of the keto oxygen. 1,4-Dihydro-lazaphosphinine are silylated to give 1,4-aza-γ
5
-phosphinines; their dibenzo derivatives (5,10-dihydrophenophosphazine oxides) require more forcing conditions (triethylsilyl bromide at 100°C) for phosphoryl silylation. These conditions are also effective for silylation of a 3-phospholene oxide.</description><subject>1,4-dihydro-1,4-azaphosphinine-1-oxides</subject><subject>1,6-dihydrophosphinine-1-oxides</subject><subject>5,10-dihydrophenophosphazine-10-oxide</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Key words</subject><subject>O-silyl 1,4-aza- γ</subject><subject>O-silyl γ</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>P derivatives</subject><subject>phosphinines</subject><subject>Preparations and properties</subject><subject>trialkylsilylation</subject><issn>1042-6507</issn><issn>1563-5325</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><recordid>eNp1j8tKw0AUhgdRsFYfwF02LqNzMndwE9LUBmKnmBTsKkwzGaikTZkUSt_eSBUX4upc-L5z-BG6B_wIWOInwDTiDCs8DDQCoBdoBIyTkJGIXQ79sA0HQFyjm77_wBiriOARkjossnyVx2Wm54GeBoV-TYPlvIjL5VtcppMgWSV5lgSLmS4Ws2yeBvo9m6TFLbpypu2bu-86RstpWiazMNcvWRLnYU0ieQhBqAg3YJ0VIInizlqo1ZobaRrGqBPSYUqtUgwoZ2JtnJFEKl5bIRqQazJGcL5b-67vfeOqvd9sjT9VgKuv6NWf6IPzcHb2pq9N67zZ1Zv-V1SEK6bEwD2fuc3OdX5rjp1vbXUwp7bzPxL5_80n09Zk_g</recordid><startdate>19900901</startdate><enddate>19900901</enddate><creator>Quin, Louis D.</creator><creator>Kisalus, John C.</creator><creator>Skolimowski, Janusch J.</creator><creator>Rao, Nandakumar S.</creator><general>Taylor & Francis Group</general><general>Taylor and Francis</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19900901</creationdate><title>O-SILYLATION OF SOME UNSATURATED CYCLIC PHOSPHINE OXIDES</title><author>Quin, Louis D. ; Kisalus, John C. ; Skolimowski, Janusch J. ; Rao, Nandakumar S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c328t-17920e1dfd718396fdd1c9b6a8ae554f78f044d99514657bafa83896cd77e18b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>1,4-dihydro-1,4-azaphosphinine-1-oxides</topic><topic>1,6-dihydrophosphinine-1-oxides</topic><topic>5,10-dihydrophenophosphazine-10-oxide</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Key words</topic><topic>O-silyl 1,4-aza- γ</topic><topic>O-silyl γ</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>P derivatives</topic><topic>phosphinines</topic><topic>Preparations and properties</topic><topic>trialkylsilylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quin, Louis D.</creatorcontrib><creatorcontrib>Kisalus, John C.</creatorcontrib><creatorcontrib>Skolimowski, Janusch J.</creatorcontrib><creatorcontrib>Rao, Nandakumar S.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Quin, Louis D.</au><au>Kisalus, John C.</au><au>Skolimowski, Janusch J.</au><au>Rao, Nandakumar S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>O-SILYLATION OF SOME UNSATURATED CYCLIC PHOSPHINE OXIDES</atitle><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle><date>1990-09-01</date><risdate>1990</risdate><volume>54</volume><issue>1-4</issue><spage>1</spage><epage>7</epage><pages>1-7</pages><issn>1042-6507</issn><eissn>1563-5325</eissn><coden>PSSLEC</coden><abstract>The phosphoryl oxygen of 1.6-dihydrophosphinine oxides is silylated rapidly at room temperature by bis(trimethylsilyl)trifluoroacetamide; the product loses a ring proton to establish the resonance stabilized γ
5
-phosphinine ring system. Similar events take place with a 3-keto derivative of a tetrahydrophosphinine oxide, which also undergoes silylation of the keto oxygen. 1,4-Dihydro-lazaphosphinine are silylated to give 1,4-aza-γ
5
-phosphinines; their dibenzo derivatives (5,10-dihydrophenophosphazine oxides) require more forcing conditions (triethylsilyl bromide at 100°C) for phosphoryl silylation. These conditions are also effective for silylation of a 3-phospholene oxide.</abstract><cop>Philadelphia, PA</cop><pub>Taylor & Francis Group</pub><doi>10.1080/10426509008042114</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1042-6507 |
| ispartof | Phosphorus, sulfur, and silicon and the related elements, 1990-09, Vol.54 (1-4), p.1-7 |
| issn | 1042-6507 1563-5325 |
| language | eng |
| recordid | cdi_pascalfrancis_primary_19369597 |
| source | Taylor & Francis Journals Complete |
| subjects | 1,4-dihydro-1,4-azaphosphinine-1-oxides 1,6-dihydrophosphinine-1-oxides 5,10-dihydrophenophosphazine-10-oxide Chemistry Exact sciences and technology Key words O-silyl 1,4-aza- γ O-silyl γ Organic chemistry Organometalloidal and organometallic compounds P derivatives phosphinines Preparations and properties trialkylsilylation |
| title | O-SILYLATION OF SOME UNSATURATED CYCLIC PHOSPHINE OXIDES |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T04%3A25%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pascalfrancis_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=O-SILYLATION%20OF%20SOME%20UNSATURATED%20CYCLIC%20PHOSPHINE%20OXIDES&rft.jtitle=Phosphorus,%20sulfur,%20and%20silicon%20and%20the%20related%20elements&rft.au=Quin,%20Louis%20D.&rft.date=1990-09-01&rft.volume=54&rft.issue=1-4&rft.spage=1&rft.epage=7&rft.pages=1-7&rft.issn=1042-6507&rft.eissn=1563-5325&rft.coden=PSSLEC&rft_id=info:doi/10.1080/10426509008042114&rft_dat=%3Cpascalfrancis_cross%3E19369597%3C/pascalfrancis_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |