1,1-Phosphinoboration of diazomethanes
The reactions of the phosphinoboranes Ph 2 PBMes 2 , Ph 2 PBpin, and Ph 2 PBcat with the diazomethanes Ph 2 CN 2 , C 12 H 8 CN 2 , and EtO 2 CCHN 2 are shown to give products of 1,1-phosphinoboration. The products ( 1-6 ) are shown to have PNB linkages with three-coordinate boron centers, whereas th...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2019, Vol.55 (8), p.121-1213 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1213 |
|---|---|
| container_issue | 8 |
| container_start_page | 121 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 55 |
| creator | Trofimova, Alina LaFortune, James H. W Qu, Zheng-Wang Westcott, Stephen A Stephan, Douglas W |
| description | The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration. The products (
1-6
) are shown to have PNB linkages with three-coordinate boron centers, whereas the products (EtOOC)CNN(PR
2
)(Bpin) (R = Ph 7,
t
Bu 8) form zwitterionic heterocycles resulting from chelation of the ester carbonyl to boron. DFT calculations show that the reactions are initiated by N-to-B addition followed by 1,2-phosphinyl shift.
The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration. |
| doi_str_mv | 10.1039/c9cc06914c |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_C9CC06914C</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2300607551</sourcerecordid><originalsourceid>FETCH-LOGICAL-c347t-d01ae7ec7b24a94802642abd20b25c342a8bb712f777cd3621a057ffd39a685a3</originalsourceid><addsrcrecordid>eNpF0DtLBDEUBeAgCq6rjb2wIFiI0bwzKSX4ggUtFOxCkkmYWdzJmMwW7q931hG9zb3Fx7lwADjF6Bojqm688h4JhZnfAzNMBYOcVe_7u5srKCnjh-ColBUaB_NqBi7wFYYvTSp903bJpWyHNnWLFBd1a7dpHYbGdqEcg4NoP0o4-d1z8HZ_96of4fL54UnfLqGnTA6wRtgGGbx0hFnFKkQEI9bVBDnCR0Js5ZzEJEopfU0FwRZxGWNNlRUVt3QOzqfcPqfPTSiDWaVN7saXhlCEBJKc41FdTsrnVEoO0fS5Xdv8ZTAyux6MVlr_9KBHfDbhXPyf---JfgPKP1fn</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2300607551</pqid></control><display><type>article</type><title>1,1-Phosphinoboration of diazomethanes</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Trofimova, Alina ; LaFortune, James H. W ; Qu, Zheng-Wang ; Westcott, Stephen A ; Stephan, Douglas W</creator><creatorcontrib>Trofimova, Alina ; LaFortune, James H. W ; Qu, Zheng-Wang ; Westcott, Stephen A ; Stephan, Douglas W</creatorcontrib><description>The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration. The products (
1-6
) are shown to have PNB linkages with three-coordinate boron centers, whereas the products (EtOOC)CNN(PR
2
)(Bpin) (R = Ph 7,
t
Bu 8) form zwitterionic heterocycles resulting from chelation of the ester carbonyl to boron. DFT calculations show that the reactions are initiated by N-to-B addition followed by 1,2-phosphinyl shift.
The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc06914c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Boron ; Carbonyls ; Chelation ; Crystallography</subject><ispartof>Chemical communications (Cambridge, England), 2019, Vol.55 (8), p.121-1213</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c347t-d01ae7ec7b24a94802642abd20b25c342a8bb712f777cd3621a057ffd39a685a3</citedby><cites>FETCH-LOGICAL-c347t-d01ae7ec7b24a94802642abd20b25c342a8bb712f777cd3621a057ffd39a685a3</cites><orcidid>0000-0001-6631-3681 ; 0000-0002-5324-2295 ; 0000-0003-4217-1038 ; 0000-0001-8140-8355</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids></links><search><creatorcontrib>Trofimova, Alina</creatorcontrib><creatorcontrib>LaFortune, James H. W</creatorcontrib><creatorcontrib>Qu, Zheng-Wang</creatorcontrib><creatorcontrib>Westcott, Stephen A</creatorcontrib><creatorcontrib>Stephan, Douglas W</creatorcontrib><title>1,1-Phosphinoboration of diazomethanes</title><title>Chemical communications (Cambridge, England)</title><description>The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration. The products (
1-6
) are shown to have PNB linkages with three-coordinate boron centers, whereas the products (EtOOC)CNN(PR
2
)(Bpin) (R = Ph 7,
t
Bu 8) form zwitterionic heterocycles resulting from chelation of the ester carbonyl to boron. DFT calculations show that the reactions are initiated by N-to-B addition followed by 1,2-phosphinyl shift.
The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration.</description><subject>Boron</subject><subject>Carbonyls</subject><subject>Chelation</subject><subject>Crystallography</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpF0DtLBDEUBeAgCq6rjb2wIFiI0bwzKSX4ggUtFOxCkkmYWdzJmMwW7q931hG9zb3Fx7lwADjF6Bojqm688h4JhZnfAzNMBYOcVe_7u5srKCnjh-ColBUaB_NqBi7wFYYvTSp903bJpWyHNnWLFBd1a7dpHYbGdqEcg4NoP0o4-d1z8HZ_96of4fL54UnfLqGnTA6wRtgGGbx0hFnFKkQEI9bVBDnCR0Js5ZzEJEopfU0FwRZxGWNNlRUVt3QOzqfcPqfPTSiDWaVN7saXhlCEBJKc41FdTsrnVEoO0fS5Xdv8ZTAyux6MVlr_9KBHfDbhXPyf---JfgPKP1fn</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Trofimova, Alina</creator><creator>LaFortune, James H. W</creator><creator>Qu, Zheng-Wang</creator><creator>Westcott, Stephen A</creator><creator>Stephan, Douglas W</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-6631-3681</orcidid><orcidid>https://orcid.org/0000-0002-5324-2295</orcidid><orcidid>https://orcid.org/0000-0003-4217-1038</orcidid><orcidid>https://orcid.org/0000-0001-8140-8355</orcidid></search><sort><creationdate>2019</creationdate><title>1,1-Phosphinoboration of diazomethanes</title><author>Trofimova, Alina ; LaFortune, James H. W ; Qu, Zheng-Wang ; Westcott, Stephen A ; Stephan, Douglas W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c347t-d01ae7ec7b24a94802642abd20b25c342a8bb712f777cd3621a057ffd39a685a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Boron</topic><topic>Carbonyls</topic><topic>Chelation</topic><topic>Crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trofimova, Alina</creatorcontrib><creatorcontrib>LaFortune, James H. W</creatorcontrib><creatorcontrib>Qu, Zheng-Wang</creatorcontrib><creatorcontrib>Westcott, Stephen A</creatorcontrib><creatorcontrib>Stephan, Douglas W</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Trofimova, Alina</au><au>LaFortune, James H. W</au><au>Qu, Zheng-Wang</au><au>Westcott, Stephen A</au><au>Stephan, Douglas W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1,1-Phosphinoboration of diazomethanes</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2019</date><risdate>2019</risdate><volume>55</volume><issue>8</issue><spage>121</spage><epage>1213</epage><pages>121-1213</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration. The products (
1-6
) are shown to have PNB linkages with three-coordinate boron centers, whereas the products (EtOOC)CNN(PR
2
)(Bpin) (R = Ph 7,
t
Bu 8) form zwitterionic heterocycles resulting from chelation of the ester carbonyl to boron. DFT calculations show that the reactions are initiated by N-to-B addition followed by 1,2-phosphinyl shift.
The reactions of the phosphinoboranes Ph
2
PBMes
2
, Ph
2
PBpin, and Ph
2
PBcat with the diazomethanes Ph
2
CN
2
, C
12
H
8
CN
2
, and EtO
2
CCHN
2
are shown to give products of 1,1-phosphinoboration.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c9cc06914c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-6631-3681</orcidid><orcidid>https://orcid.org/0000-0002-5324-2295</orcidid><orcidid>https://orcid.org/0000-0003-4217-1038</orcidid><orcidid>https://orcid.org/0000-0001-8140-8355</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2019, Vol.55 (8), p.121-1213 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_C9CC06914C |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Boron Carbonyls Chelation Crystallography |
| title | 1,1-Phosphinoboration of diazomethanes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-22T16%3A11%3A03IST&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=1,1-Phosphinoboration%20of%20diazomethanes&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Trofimova,%20Alina&rft.date=2019&rft.volume=55&rft.issue=8&rft.spage=121&rft.epage=1213&rft.pages=121-1213&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c9cc06914c&rft_dat=%3Cproquest_cross%3E2300607551%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=2300607551&rft_id=info:pmid/&rfr_iscdi=true |