Synthesis and Rearrangement of Intramolecularly Stabilized 1.sigma.2,3.sigma.2-Diphosphaallylic Cations into Intramolecularly Stabilized 1.sigma.1,3.sigma.3-Diphosphaallylic Cations

Synthesis and Rearrangement of Intramolecularly Stabilized 1.sigma.2,3.sigma.2-Diphosphaallylic Cations into Intramolecularly Stabilized 1.sigma.1,3.sigma.3-Diphosphaallylic Cations

Two equivalents of boron trifluoride-diethyl ether complex or 1 equiv of trifluoromethanesulfonic acid reacts with C-[bis(diisopropylamino)phosphino]-C,P-bis(diisopropylamino)phosphaalkene 1, cleaving one of the diisopropylamino substituents at the

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Veröffentlicht in:Journal of the American Chemical Society 1994-07, Vol.116 (14), p.6149-6152
Hauptverfasser: Soleilhavoup, Michele, Canac, Yves, Polozov, Alexander M, Baceiredo, Antoine, Bertrand, Guy
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Coordination chemistry
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container_end_page 6152
container_issue 14
container_start_page 6149
container_title Journal of the American Chemical Society
container_volume 116
creator Soleilhavoup, Michele
Canac, Yves
Polozov, Alexander M
Baceiredo, Antoine
Bertrand, Guy
description Two equivalents of boron trifluoride-diethyl ether complex or 1 equiv of trifluoromethanesulfonic acid reacts with C-[bis(diisopropylamino)phosphino]-C,P-bis(diisopropylamino)phosphaalkene 1, cleaving one of the diisopropylamino substituents at the
doi_str_mv 10.1021/ja00093a012
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This affords the corresponding 1 2,3 a2-diphosphaallylic cation 4,which is isolated as the four-membered-heterocycle 3. Addition of a catalytic amount of base to 3 leads to a 1 *,3 3-diphosphaallylic cation 5, which is isolated as the diphosphirenium salt 2. Mesityllithium and the lithium salts of diisopropylamine or dicyclohexylamine react at the &lt;r2-phosphorus atom of the cationic heterocycles 2 and 3, affording the corresponding phosphaalkenes 8, 1, and 6, respectively. All the results demonstrate the high electrophilicity of low-coordinated diphosphaallylic cations, which are only isolable as intramolecular donor-acceptor complexes.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja00093a012</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Chemical Sciences ; Coordination chemistry</subject><ispartof>Journal of the American Chemical Society, 1994-07, Vol.116 (14), p.6149-6152</ispartof><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a182D-42707a164fc13754c72f9df360276f31d7c7ec9b46c1c633b221e2171248ea393</citedby><orcidid>0000-0002-6428-9697 ; 0000-0002-3747-554X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja00093a012$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja00093a012$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,777,781,882,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03739862$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Soleilhavoup, Michele</creatorcontrib><creatorcontrib>Canac, Yves</creatorcontrib><creatorcontrib>Polozov, Alexander M</creatorcontrib><creatorcontrib>Baceiredo, Antoine</creatorcontrib><creatorcontrib>Bertrand, Guy</creatorcontrib><title>Synthesis and Rearrangement of Intramolecularly Stabilized 1.sigma.2,3.sigma.2-Diphosphaallylic Cations into Intramolecularly Stabilized 1.sigma.1,3.sigma.3-Diphosphaallylic Cations</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Two equivalents of boron trifluoride-diethyl ether complex or 1 equiv of trifluoromethanesulfonic acid reacts with C-[bis(diisopropylamino)phosphino]-C,P-bis(diisopropylamino)phosphaalkene 1, cleaving one of the diisopropylamino substituents at the &lt;r3-phosphorus atom. This affords the corresponding 1 2,3 a2-diphosphaallylic cation 4,which is isolated as the four-membered-heterocycle 3. Addition of a catalytic amount of base to 3 leads to a 1 *,3 3-diphosphaallylic cation 5, which is isolated as the diphosphirenium salt 2. Mesityllithium and the lithium salts of diisopropylamine or dicyclohexylamine react at the &lt;r2-phosphorus atom of the cationic heterocycles 2 and 3, affording the corresponding phosphaalkenes 8, 1, and 6, respectively. All the results demonstrate the high electrophilicity of low-coordinated diphosphaallylic cations, which are only isolable as intramolecular donor-acceptor complexes.</description><subject>Chemical Sciences</subject><subject>Coordination chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><recordid>eNqNkc1KAzEQgIMoWKsnX2BvIro1k2yT3aN0_aVUsXoO0zTbpqa7JdmK9b18P1eqxYOCp_nhm48ZhpBDoB2gDM5mSCnNOFJgW6QFXUbjLjCxTVpNn8UyFXyX7IUwa8qEpdAi78NVWU9NsCHCchw9GPQey4mZm7KOqiK6KWuP88oZvXTo3Soa1jiyzr6ZcQSdYCdz7LBT_p3FuV1Mq7CYIjq3clZHPaxtVYbIlnX1LxtsbPxP2z7ZKdAFc_AV2-Tp8uKxdx33765ueuf9GCFleZwwSSWCSAoNXHYTLVmRjQsuKJOi4DCWWhqdjRKhQQvOR4yBYSCBJalBnvE2OV57p-jUwts5-pWq0Krr87767FEueZYK9gINe7Jmta9C8KbYDABVn99RP77T0PGatqE2rxsU_bMSstlVPd4P1eBW5HwgcpU3_NGaRx3UrFr6srn7V_MHJjiexg</recordid><startdate>19940701</startdate><enddate>19940701</enddate><creator>Soleilhavoup, Michele</creator><creator>Canac, Yves</creator><creator>Polozov, Alexander M</creator><creator>Baceiredo, Antoine</creator><creator>Bertrand, Guy</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-6428-9697</orcidid><orcidid>https://orcid.org/0000-0002-3747-554X</orcidid></search><sort><creationdate>19940701</creationdate><title>Synthesis and Rearrangement of Intramolecularly Stabilized 1.sigma.2,3.sigma.2-Diphosphaallylic Cations into Intramolecularly Stabilized 1.sigma.1,3.sigma.3-Diphosphaallylic Cations</title><author>Soleilhavoup, Michele ; Canac, Yves ; Polozov, Alexander M ; Baceiredo, Antoine ; Bertrand, Guy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a182D-42707a164fc13754c72f9df360276f31d7c7ec9b46c1c633b221e2171248ea393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>Chemical Sciences</topic><topic>Coordination chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Soleilhavoup, Michele</creatorcontrib><creatorcontrib>Canac, Yves</creatorcontrib><creatorcontrib>Polozov, Alexander M</creatorcontrib><creatorcontrib>Baceiredo, Antoine</creatorcontrib><creatorcontrib>Bertrand, Guy</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Soleilhavoup, Michele</au><au>Canac, Yves</au><au>Polozov, Alexander M</au><au>Baceiredo, Antoine</au><au>Bertrand, Guy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Rearrangement of Intramolecularly Stabilized 1.sigma.2,3.sigma.2-Diphosphaallylic Cations into Intramolecularly Stabilized 1.sigma.1,3.sigma.3-Diphosphaallylic Cations</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>1994-07-01</date><risdate>1994</risdate><volume>116</volume><issue>14</issue><spage>6149</spage><epage>6152</epage><pages>6149-6152</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Two equivalents of boron trifluoride-diethyl ether complex or 1 equiv of trifluoromethanesulfonic acid reacts with C-[bis(diisopropylamino)phosphino]-C,P-bis(diisopropylamino)phosphaalkene 1, cleaving one of the diisopropylamino substituents at the &lt;r3-phosphorus atom. This affords the corresponding 1 2,3 a2-diphosphaallylic cation 4,which is isolated as the four-membered-heterocycle 3. Addition of a catalytic amount of base to 3 leads to a 1 *,3 3-diphosphaallylic cation 5, which is isolated as the diphosphirenium salt 2. Mesityllithium and the lithium salts of diisopropylamine or dicyclohexylamine react at the &lt;r2-phosphorus atom of the cationic heterocycles 2 and 3, affording the corresponding phosphaalkenes 8, 1, and 6, respectively. All the results demonstrate the high electrophilicity of low-coordinated diphosphaallylic cations, which are only isolable as intramolecular donor-acceptor complexes.</abstract><pub>American Chemical Society</pub><doi>10.1021/ja00093a012</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-6428-9697</orcidid><orcidid>https://orcid.org/0000-0002-3747-554X</orcidid></addata></record>
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Coordination chemistry
title Synthesis and Rearrangement of Intramolecularly Stabilized 1.sigma.2,3.sigma.2-Diphosphaallylic Cations into Intramolecularly Stabilized 1.sigma.1,3.sigma.3-Diphosphaallylic Cations
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