Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1-Alkenes and Their Application in Synthesis
1‐Alkenes are converted in high yields to the corresponding primary diorganomagnesium compounds by transition metalcatalyzed hydromagnesation reaction using catalytically prepared suspended (MgH2*) or dissolved magnesium hydride (MgH2*). The most active hydromagnesation catalysts have been found to...
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| Veröffentlicht in: | Chemische Berichte 1993-06, Vol.126 (6), p.1371-1383 |
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| container_title | Chemische Berichte |
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| creator | Bogdanović, Borislav Bons, Peter Konstantinović, Stanimir Schwickardi, Manfred Westeppe, Uwe |
| description | 1‐Alkenes are converted in high yields to the corresponding primary diorganomagnesium compounds by transition metalcatalyzed hydromagnesation reaction using catalytically prepared suspended (MgH2*) or dissolved magnesium hydride (MgH2*). The most active hydromagnesation catalysts have been found to be combinations of zirconium tetrahalides with MgH2* or MgH2*. The reaction is highly regio‐and chemoselective. The diorganomagnesium compounds prepared in situ from magnesium, hydrogen, and 1‐alkenes can be applied to the synthesis of organic and organometallic compounds just as Grignard compounds (Scheme 3, reaction 3–11). Dioctylmagnesium undergoes the growth reaction with ethene in the presence of quinuclidine and is oxidized by molecular oxygen in high yield to 1‐octanol. |
| doi_str_mv | 10.1002/cber.19931260616 |
| format | Article |
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The most active hydromagnesation catalysts have been found to be combinations of zirconium tetrahalides with MgH2* or MgH2*. The reaction is highly regio‐and chemoselective. The diorganomagnesium compounds prepared in situ from magnesium, hydrogen, and 1‐alkenes can be applied to the synthesis of organic and organometallic compounds just as Grignard compounds (Scheme 3, reaction 3–11). Dioctylmagnesium undergoes the growth reaction with ethene in the presence of quinuclidine and is oxidized by molecular oxygen in high yield to 1‐octanol.</description><identifier>ISSN: 0009-2940</identifier><identifier>EISSN: 1099-0682</identifier><identifier>DOI: 10.1002/cber.19931260616</identifier><identifier>CODEN: CHBEAM</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>application in syntheses ; catalytically prepared ; Chemistry ; diorgano compounds ; Exact sciences and technology ; hydrogen and 1-alkenes ; Hydromagnesation reactions ; Magnesium ; Magnesium hydride ; Magnesium hydride, catalytically prepared ; Magnesium, diorgano compounds, application in syntheses ; Magnesium, diorgano compounds, oxidation of ; Magnesium, diorgano compounds, preparation from magnesium, hydrogen and 1‐alkenes ; Organic chemistry ; oxidation of ; preparation from magnesium</subject><ispartof>Chemische Berichte, 1993-06, Vol.126 (6), p.1371-1383</ispartof><rights>Copyright © 1993 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3626-aac809e767a145ab7414a1281741e28ae98bd812ea956ffa89e2a8788a8824c73</citedby><cites>FETCH-LOGICAL-c3626-aac809e767a145ab7414a1281741e28ae98bd812ea956ffa89e2a8788a8824c73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcber.19931260616$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcber.19931260616$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4884441$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Bogdanović, Borislav</creatorcontrib><creatorcontrib>Bons, Peter</creatorcontrib><creatorcontrib>Konstantinović, Stanimir</creatorcontrib><creatorcontrib>Schwickardi, Manfred</creatorcontrib><creatorcontrib>Westeppe, Uwe</creatorcontrib><title>Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1-Alkenes and Their Application in Synthesis</title><title>Chemische Berichte</title><addtitle>Chem. Ber</addtitle><description>1‐Alkenes are converted in high yields to the corresponding primary diorganomagnesium compounds by transition metalcatalyzed hydromagnesation reaction using catalytically prepared suspended (MgH2*) or dissolved magnesium hydride (MgH2*). The most active hydromagnesation catalysts have been found to be combinations of zirconium tetrahalides with MgH2* or MgH2*. The reaction is highly regio‐and chemoselective. The diorganomagnesium compounds prepared in situ from magnesium, hydrogen, and 1‐alkenes can be applied to the synthesis of organic and organometallic compounds just as Grignard compounds (Scheme 3, reaction 3–11). Dioctylmagnesium undergoes the growth reaction with ethene in the presence of quinuclidine and is oxidized by molecular oxygen in high yield to 1‐octanol.</description><subject>application in syntheses</subject><subject>catalytically prepared</subject><subject>Chemistry</subject><subject>diorgano compounds</subject><subject>Exact sciences and technology</subject><subject>hydrogen and 1-alkenes</subject><subject>Hydromagnesation reactions</subject><subject>Magnesium</subject><subject>Magnesium hydride</subject><subject>Magnesium hydride, catalytically prepared</subject><subject>Magnesium, diorgano compounds, application in syntheses</subject><subject>Magnesium, diorgano compounds, oxidation of</subject><subject>Magnesium, diorgano compounds, preparation from magnesium, hydrogen and 1‐alkenes</subject><subject>Organic chemistry</subject><subject>oxidation of</subject><subject>preparation from magnesium</subject><issn>0009-2940</issn><issn>1099-0682</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAQxS0EEqWwM3pgJMV2XMceGEqAFql8iA_BZl1TpxgSJ7JbQf57UgIIJqa703u_d9JDaJ-SASWEHWUz4wdUqZgyQQQVG6hHiVIREZJtoh4hREVMcbKNdkJ4ISTmiYh7KD-1lV-Aq0pYOBPsqsRpVdbVys0Dzn1V4stv4RBPmrmvFsYdYnBzTKNR8Wpa7fO6fzbW41FdFzaDpa0ctg7fNW753MJhF23lUASz9zX76OH87D6dRNPr8UU6mkZZLJiIADJJlElEApQPYZZwyoEySdvFMAlGydlcUmZADUWeg1SGgUykBCkZz5K4j0iXm_kqBG9yXXtbgm80JXrdk173pH_11CIHHVJDyKDIPbjMhh-OS8k5p63tuLO92cI0_8bq9OTs9u-bqONtWJr3Hx78qxZJnAz149VY8_NHfpM-UX0SfwBmjYnq</recordid><startdate>199306</startdate><enddate>199306</enddate><creator>Bogdanović, Borislav</creator><creator>Bons, Peter</creator><creator>Konstantinović, Stanimir</creator><creator>Schwickardi, Manfred</creator><creator>Westeppe, Uwe</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199306</creationdate><title>Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1-Alkenes and Their Application in Synthesis</title><author>Bogdanović, Borislav ; Bons, Peter ; Konstantinović, Stanimir ; Schwickardi, Manfred ; Westeppe, Uwe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3626-aac809e767a145ab7414a1281741e28ae98bd812ea956ffa89e2a8788a8824c73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>application in syntheses</topic><topic>catalytically prepared</topic><topic>Chemistry</topic><topic>diorgano compounds</topic><topic>Exact sciences and technology</topic><topic>hydrogen and 1-alkenes</topic><topic>Hydromagnesation reactions</topic><topic>Magnesium</topic><topic>Magnesium hydride</topic><topic>Magnesium hydride, catalytically prepared</topic><topic>Magnesium, diorgano compounds, application in syntheses</topic><topic>Magnesium, diorgano compounds, oxidation of</topic><topic>Magnesium, diorgano compounds, preparation from magnesium, hydrogen and 1‐alkenes</topic><topic>Organic chemistry</topic><topic>oxidation of</topic><topic>preparation from magnesium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bogdanović, Borislav</creatorcontrib><creatorcontrib>Bons, Peter</creatorcontrib><creatorcontrib>Konstantinović, Stanimir</creatorcontrib><creatorcontrib>Schwickardi, Manfred</creatorcontrib><creatorcontrib>Westeppe, Uwe</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemische Berichte</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bogdanović, Borislav</au><au>Bons, Peter</au><au>Konstantinović, Stanimir</au><au>Schwickardi, Manfred</au><au>Westeppe, Uwe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1-Alkenes and Their Application in Synthesis</atitle><jtitle>Chemische Berichte</jtitle><addtitle>Chem. Ber</addtitle><date>1993-06</date><risdate>1993</risdate><volume>126</volume><issue>6</issue><spage>1371</spage><epage>1383</epage><pages>1371-1383</pages><issn>0009-2940</issn><eissn>1099-0682</eissn><coden>CHBEAM</coden><abstract>1‐Alkenes are converted in high yields to the corresponding primary diorganomagnesium compounds by transition metalcatalyzed hydromagnesation reaction using catalytically prepared suspended (MgH2*) or dissolved magnesium hydride (MgH2*). The most active hydromagnesation catalysts have been found to be combinations of zirconium tetrahalides with MgH2* or MgH2*. The reaction is highly regio‐and chemoselective. The diorganomagnesium compounds prepared in situ from magnesium, hydrogen, and 1‐alkenes can be applied to the synthesis of organic and organometallic compounds just as Grignard compounds (Scheme 3, reaction 3–11). Dioctylmagnesium undergoes the growth reaction with ethene in the presence of quinuclidine and is oxidized by molecular oxygen in high yield to 1‐octanol.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/cber.19931260616</doi><tpages>13</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2940 |
| ispartof | Chemische Berichte, 1993-06, Vol.126 (6), p.1371-1383 |
| issn | 0009-2940 1099-0682 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_cber_19931260616 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | application in syntheses catalytically prepared Chemistry diorgano compounds Exact sciences and technology hydrogen and 1-alkenes Hydromagnesation reactions Magnesium Magnesium hydride Magnesium hydride, catalytically prepared Magnesium, diorgano compounds, application in syntheses Magnesium, diorgano compounds, oxidation of Magnesium, diorgano compounds, preparation from magnesium, hydrogen and 1‐alkenes Organic chemistry oxidation of preparation from magnesium |
| title | Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1-Alkenes and Their Application in Synthesis |
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