An NMR study of the structure and reactivity of phosphonium ylides stabilized by a carbonyl function
The structures of five stabilized phosphonium ylides 1 - 5 were studied by 1 H, 13 C, and 31 P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminan...
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| Veröffentlicht in: | Canadian journal of chemistry 1991-12, Vol.69 (12), p.1929-1939 |
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| container_end_page | 1939 |
|---|---|
| container_issue | 12 |
| container_start_page | 1929 |
| container_title | Canadian journal of chemistry |
| container_volume | 69 |
| creator | Kayser, Margaret M Hatt, Krista L Hooper, Donald L |
| description | The structures of five stabilized phosphonium ylides
1
-
5
were studied by
1
H,
13
C, and
31
P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminants (conjugate acids, H
2
O, etc.) on the structure and reactivity of these compounds, is discussed. Key words: stabilized phosphoranes, Wittig condensations, acid catalysis. |
| doi_str_mv | 10.1139/v91-278 |
| format | Article |
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1
-
5
were studied by
1
H,
13
C, and
31
P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminants (conjugate acids, H
2
O, etc.) on the structure and reactivity of these compounds, is discussed. Key words: stabilized phosphoranes, Wittig condensations, acid catalysis.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v91-278</identifier><identifier>CODEN: CJCHAG</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><subject>Chemistry ; Exact sciences and technology ; Organic chemistry ; Organometalloidal and organometallic compounds ; P derivatives ; Preparations and properties</subject><ispartof>Canadian journal of chemistry, 1991-12, Vol.69 (12), p.1929-1939</ispartof><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c349t-aeb376b84f766b699f521efa2b081ae221b9105fa857ef9437e208651eb9446a3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v91-278$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v91-278$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,780,784,2932,27924,27925,64428,65234</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5270211$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kayser, Margaret M</creatorcontrib><creatorcontrib>Hatt, Krista L</creatorcontrib><creatorcontrib>Hooper, Donald L</creatorcontrib><title>An NMR study of the structure and reactivity of phosphonium ylides stabilized by a carbonyl function</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>The structures of five stabilized phosphonium ylides
1
-
5
were studied by
1
H,
13
C, and
31
P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminants (conjugate acids, H
2
O, etc.) on the structure and reactivity of these compounds, is discussed. Key words: stabilized phosphoranes, Wittig condensations, acid catalysis.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>P derivatives</subject><subject>Preparations and properties</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><recordid>eNp1kFtLxDAQhYMouFbxL-RBFIRqkqaXPC6LN1gVRJ_LJE3YSDctSbtQf73RXfZB8GEYDvOdM3AQOqfkhtJM3G4ETVlZHaAZ5RVJMyboIZoRQqqUE86O0UkIn1GWhOUz1Mwdfnl-w2EYmwl3Bg8rHYUf1TB6jcE12GtQg93Y4ffer7oQx9lxjafWNjpEHKRt7ZdusJwwYAVedm5qsRlddHbuFB0ZaIM-2-0EfdzfvS8e0-Xrw9NivkxVxsWQgpZZWciKm7IoZCGEyRnVBpgkFQXNGJWCktxAlZfaCJ6VmpGqyKmWgvMCsgRdbXOV70Lw2tS9t2vwU01J_VNOHcupYzmRvNiSPQQFrfHglA17PGexnWhI0OUWc155HTR4tdpDu6y6b0wEr_8H_z7_BmdOgDk</recordid><startdate>19911201</startdate><enddate>19911201</enddate><creator>Kayser, Margaret M</creator><creator>Hatt, Krista L</creator><creator>Hooper, Donald L</creator><general>NRC Research Press</general><general>National Research Council of Canada</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19911201</creationdate><title>An NMR study of the structure and reactivity of phosphonium ylides stabilized by a carbonyl function</title><author>Kayser, Margaret M ; Hatt, Krista L ; Hooper, Donald L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c349t-aeb376b84f766b699f521efa2b081ae221b9105fa857ef9437e208651eb9446a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>P derivatives</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kayser, Margaret M</creatorcontrib><creatorcontrib>Hatt, Krista L</creatorcontrib><creatorcontrib>Hooper, Donald L</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kayser, Margaret M</au><au>Hatt, Krista L</au><au>Hooper, Donald L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An NMR study of the structure and reactivity of phosphonium ylides stabilized by a carbonyl function</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1991-12-01</date><risdate>1991</risdate><volume>69</volume><issue>12</issue><spage>1929</spage><epage>1939</epage><pages>1929-1939</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><coden>CJCHAG</coden><abstract>The structures of five stabilized phosphonium ylides
1
-
5
were studied by
1
H,
13
C, and
31
P NMR. Various trapping experiments were followed by investigation of the relative reactivities of these ylides vis-à-vis benzaldehyde. A novel effect of some significance, the influence of acidic contaminants (conjugate acids, H
2
O, etc.) on the structure and reactivity of these compounds, is discussed. Key words: stabilized phosphoranes, Wittig condensations, acid catalysis.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v91-278</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Canadian journal of chemistry, 1991-12, Vol.69 (12), p.1929-1939 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_crossref_primary_10_1139_v91_278 |
| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Chemistry Exact sciences and technology Organic chemistry Organometalloidal and organometallic compounds P derivatives Preparations and properties |
| title | An NMR study of the structure and reactivity of phosphonium ylides stabilized by a carbonyl function |
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