Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics

Lithium−halogen exchange of (Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene (1) and subsequent addition to (η4-1,5-cod)PtCl2 yields the platinabenzene (η5-C5H3Ph2)[PtC5H3Ph2] (7), in which the metallacyclic ring and C5H3Ph2 (Cp′) unit are both derived from the cyclopropene skeleton. Starting instead...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organometallics 2009-09, Vol.28 (17), p.5183-5190
Hauptverfasser: Jacob, Volker, Landorf, Christopher W, Zakharov, Lev N, Weakley, Timothy J. R, Haley, Michael M
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5190
container_issue 17
container_start_page 5183
container_title Organometallics
container_volume 28
creator Jacob, Volker
Landorf, Christopher W
Zakharov, Lev N
Weakley, Timothy J. R
Haley, Michael M
description Lithium−halogen exchange of (Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene (1) and subsequent addition to (η4-1,5-cod)PtCl2 yields the platinabenzene (η5-C5H3Ph2)[PtC5H3Ph2] (7), in which the metallacyclic ring and C5H3Ph2 (Cp′) unit are both derived from the cyclopropene skeleton. Starting instead with (η5-C5Me5)Pt(CO)I, treatment with three nucleophilic (Z)-3-(2-lithiovinyl)cyclopropenes provides platinabenzenes (η5-C5Me5)[PtC5H3PhR] (R = Ph (8), t-Bu (9), Me (10)) in low to modest yield. All platinabenzenes have been fully characterized by NMR spectroscopy and X-ray crystallography. Intermediate σ-vinyl complexes (η5-C5Me5)Pt(σ-C5H3PhR) (R = Ph (14), t-Bu (15)) are also isolated from the reaction mixtures and convert cleanly to the corresponding platinabenzenes in near quantitative yield. Reactivity studies of (η5-C5Me5)[PtC5H3Ph2] with a variety of reagents/conditions are also reported.
doi_str_mv 10.1021/om900439z
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_om900439z</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>g35803804</sourcerecordid><originalsourceid>FETCH-LOGICAL-a259t-cafc8c0662f6d1ae6da488afb75c3b866ee0e2eb3ebc4a933e9af7849ed2646a3</originalsourceid><addsrcrecordid>eNptkEtLw0AUhQdRMFYX_oPZuBCM3plJJ4k7Cb6gYml1HW4mdzAljzIzFdpfb7TiytW55_BxuBzGzgVcC5DiZuhygETluwMWiamEWEMiDlkEMtVxqpQ6ZiferwBAp0pGzMxbDE2PFfU76snf8uW2Dx_kG3_F525YkwsNjTf2NV8QmtB8NmHLl2FTjzkfLEe-QEe8aNH_-BcK2LYYoxu6sdv4U3ZksfV09qsT9v5w_1Y8xbPXx-fibhajnOYhNmhNZkBraXUtkHSNSZahrdKpUVWmNRGQpEpRZRLMlaIcbZolOdVSJxrVhF3ue40bvHdky7VrOnTbUkD5vU75t87IXuxZNL5cDRvXj5_9w30BLrFl7g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics</title><source>American Chemical Society Journals</source><creator>Jacob, Volker ; Landorf, Christopher W ; Zakharov, Lev N ; Weakley, Timothy J. R ; Haley, Michael M</creator><creatorcontrib>Jacob, Volker ; Landorf, Christopher W ; Zakharov, Lev N ; Weakley, Timothy J. R ; Haley, Michael M</creatorcontrib><description>Lithium−halogen exchange of (Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene (1) and subsequent addition to (η4-1,5-cod)PtCl2 yields the platinabenzene (η5-C5H3Ph2)[PtC5H3Ph2] (7), in which the metallacyclic ring and C5H3Ph2 (Cp′) unit are both derived from the cyclopropene skeleton. Starting instead with (η5-C5Me5)Pt(CO)I, treatment with three nucleophilic (Z)-3-(2-lithiovinyl)cyclopropenes provides platinabenzenes (η5-C5Me5)[PtC5H3PhR] (R = Ph (8), t-Bu (9), Me (10)) in low to modest yield. All platinabenzenes have been fully characterized by NMR spectroscopy and X-ray crystallography. Intermediate σ-vinyl complexes (η5-C5Me5)Pt(σ-C5H3PhR) (R = Ph (14), t-Bu (15)) are also isolated from the reaction mixtures and convert cleanly to the corresponding platinabenzenes in near quantitative yield. Reactivity studies of (η5-C5Me5)[PtC5H3Ph2] with a variety of reagents/conditions are also reported.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/om900439z</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organometallics, 2009-09, Vol.28 (17), p.5183-5190</ispartof><rights>Copyright © 2009 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a259t-cafc8c0662f6d1ae6da488afb75c3b866ee0e2eb3ebc4a933e9af7849ed2646a3</citedby><cites>FETCH-LOGICAL-a259t-cafc8c0662f6d1ae6da488afb75c3b866ee0e2eb3ebc4a933e9af7849ed2646a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/om900439z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/om900439z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Jacob, Volker</creatorcontrib><creatorcontrib>Landorf, Christopher W</creatorcontrib><creatorcontrib>Zakharov, Lev N</creatorcontrib><creatorcontrib>Weakley, Timothy J. R</creatorcontrib><creatorcontrib>Haley, Michael M</creatorcontrib><title>Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics</title><title>Organometallics</title><addtitle>Organometallics</addtitle><description>Lithium−halogen exchange of (Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene (1) and subsequent addition to (η4-1,5-cod)PtCl2 yields the platinabenzene (η5-C5H3Ph2)[PtC5H3Ph2] (7), in which the metallacyclic ring and C5H3Ph2 (Cp′) unit are both derived from the cyclopropene skeleton. Starting instead with (η5-C5Me5)Pt(CO)I, treatment with three nucleophilic (Z)-3-(2-lithiovinyl)cyclopropenes provides platinabenzenes (η5-C5Me5)[PtC5H3PhR] (R = Ph (8), t-Bu (9), Me (10)) in low to modest yield. All platinabenzenes have been fully characterized by NMR spectroscopy and X-ray crystallography. Intermediate σ-vinyl complexes (η5-C5Me5)Pt(σ-C5H3PhR) (R = Ph (14), t-Bu (15)) are also isolated from the reaction mixtures and convert cleanly to the corresponding platinabenzenes in near quantitative yield. Reactivity studies of (η5-C5Me5)[PtC5H3Ph2] with a variety of reagents/conditions are also reported.</description><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNptkEtLw0AUhQdRMFYX_oPZuBCM3plJJ4k7Cb6gYml1HW4mdzAljzIzFdpfb7TiytW55_BxuBzGzgVcC5DiZuhygETluwMWiamEWEMiDlkEMtVxqpQ6ZiferwBAp0pGzMxbDE2PFfU76snf8uW2Dx_kG3_F525YkwsNjTf2NV8QmtB8NmHLl2FTjzkfLEe-QEe8aNH_-BcK2LYYoxu6sdv4U3ZksfV09qsT9v5w_1Y8xbPXx-fibhajnOYhNmhNZkBraXUtkHSNSZahrdKpUVWmNRGQpEpRZRLMlaIcbZolOdVSJxrVhF3ue40bvHdky7VrOnTbUkD5vU75t87IXuxZNL5cDRvXj5_9w30BLrFl7g</recordid><startdate>20090914</startdate><enddate>20090914</enddate><creator>Jacob, Volker</creator><creator>Landorf, Christopher W</creator><creator>Zakharov, Lev N</creator><creator>Weakley, Timothy J. R</creator><creator>Haley, Michael M</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20090914</creationdate><title>Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics</title><author>Jacob, Volker ; Landorf, Christopher W ; Zakharov, Lev N ; Weakley, Timothy J. R ; Haley, Michael M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a259t-cafc8c0662f6d1ae6da488afb75c3b866ee0e2eb3ebc4a933e9af7849ed2646a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jacob, Volker</creatorcontrib><creatorcontrib>Landorf, Christopher W</creatorcontrib><creatorcontrib>Zakharov, Lev N</creatorcontrib><creatorcontrib>Weakley, Timothy J. R</creatorcontrib><creatorcontrib>Haley, Michael M</creatorcontrib><collection>CrossRef</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jacob, Volker</au><au>Landorf, Christopher W</au><au>Zakharov, Lev N</au><au>Weakley, Timothy J. R</au><au>Haley, Michael M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics</atitle><jtitle>Organometallics</jtitle><addtitle>Organometallics</addtitle><date>2009-09-14</date><risdate>2009</risdate><volume>28</volume><issue>17</issue><spage>5183</spage><epage>5190</epage><pages>5183-5190</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>Lithium−halogen exchange of (Z)-1,2-diphenyl-3-(2-iodoethenyl)cyclopropene (1) and subsequent addition to (η4-1,5-cod)PtCl2 yields the platinabenzene (η5-C5H3Ph2)[PtC5H3Ph2] (7), in which the metallacyclic ring and C5H3Ph2 (Cp′) unit are both derived from the cyclopropene skeleton. Starting instead with (η5-C5Me5)Pt(CO)I, treatment with three nucleophilic (Z)-3-(2-lithiovinyl)cyclopropenes provides platinabenzenes (η5-C5Me5)[PtC5H3PhR] (R = Ph (8), t-Bu (9), Me (10)) in low to modest yield. All platinabenzenes have been fully characterized by NMR spectroscopy and X-ray crystallography. Intermediate σ-vinyl complexes (η5-C5Me5)Pt(σ-C5H3PhR) (R = Ph (14), t-Bu (15)) are also isolated from the reaction mixtures and convert cleanly to the corresponding platinabenzenes in near quantitative yield. Reactivity studies of (η5-C5Me5)[PtC5H3Ph2] with a variety of reagents/conditions are also reported.</abstract><pub>American Chemical Society</pub><doi>10.1021/om900439z</doi><tpages>8</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0276-7333
ispartof Organometallics, 2009-09, Vol.28 (17), p.5183-5190
issn 0276-7333
1520-6041
language eng
recordid cdi_crossref_primary_10_1021_om900439z
source American Chemical Society Journals
title Platinabenzenes: Synthesis, Properties, and Reactivity Studies of a Rare Class of Metalla-aromatics
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T14%3A18%3A12IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Platinabenzenes:%20Synthesis,%20Properties,%20and%20Reactivity%20Studies%20of%20a%20Rare%20Class%20of%20Metalla-aromatics&rft.jtitle=Organometallics&rft.au=Jacob,%20Volker&rft.date=2009-09-14&rft.volume=28&rft.issue=17&rft.spage=5183&rft.epage=5190&rft.pages=5183-5190&rft.issn=0276-7333&rft.eissn=1520-6041&rft_id=info:doi/10.1021/om900439z&rft_dat=%3Cacs_cross%3Eg35803804%3C/acs_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