Et2Zn-Mediated Rearrangement of Bromohydrins
A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room temperature for 2 h, followed by 1,2-migration to give t...
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| Veröffentlicht in: | Journal of organic chemistry 2008-05, Vol.73 (9), p.3516-3522 |
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| container_title | Journal of organic chemistry |
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| creator | Li, Lezhen Cai, Peijie Guo, Qingxiang Xue, Song |
| description | A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated. |
| doi_str_mv | 10.1021/jo800231s |
| format | Article |
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Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo800231s</identifier><identifier>PMID: 18380443</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2008-05, Vol.73 (9), p.3516-3522</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo800231s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo800231s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20301174$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18380443$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Lezhen</creatorcontrib><creatorcontrib>Cai, Peijie</creatorcontrib><creatorcontrib>Guo, Qingxiang</creatorcontrib><creatorcontrib>Xue, Song</creatorcontrib><title>Et2Zn-Mediated Rearrangement of Bromohydrins</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNpFkctOwzAQRS0EoqWw4AdQN7AiYHtiJ15C1QJSeaiUDRvLcSaQkkexE4n-PalaymxGmjm6mjuXkFNGrxjl7HpRx5RyYH6P9JngNJCKhvuk3w15AFxCjxx5v6BdCSEOSY_FENMwhD65HDf8vQoeMc1Ng-lwhsY5U31giVUzrLPhravL-nOVurzyx-QgM4XHk20fkLfJeD66D6bPdw-jm2lgOOdNkFIhIREqwTCLlVLcRgnFyArKWAqcC5bIOJMQgcqAqxgSTFHYzFqFHA2FAbnY6C5d_d2ib3SZe4tFYSqsW6-lYiGsfQ3I2RZskxJTvXR5adxK__nrgPMtYLw1RdZZs7nfcZxCd1MUdlyw4XLf4M9ub9yXlhFEQs9fXvUTTMOJmkg9-9c11utF3bqq-4dmVK_z0Ls84BcvsHcI</recordid><startdate>20080502</startdate><enddate>20080502</enddate><creator>Li, Lezhen</creator><creator>Cai, Peijie</creator><creator>Guo, Qingxiang</creator><creator>Xue, Song</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20080502</creationdate><title>Et2Zn-Mediated Rearrangement of Bromohydrins</title><author>Li, Lezhen ; Cai, Peijie ; Guo, Qingxiang ; Xue, Song</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a222t-d0563b59be4f89992c7b0e7c5011d32251b68f63739f32983bede5cfcc9e2ea03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Lezhen</creatorcontrib><creatorcontrib>Cai, Peijie</creatorcontrib><creatorcontrib>Guo, Qingxiang</creatorcontrib><creatorcontrib>Xue, Song</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Lezhen</au><au>Cai, Peijie</au><au>Guo, Qingxiang</au><au>Xue, Song</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Et2Zn-Mediated Rearrangement of Bromohydrins</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-05-02</date><risdate>2008</risdate><volume>73</volume><issue>9</issue><spage>3516</spage><epage>3522</epage><pages>3516-3522</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18380443</pmid><doi>10.1021/jo800231s</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Organic chemistry Preparations and properties |
| title | Et2Zn-Mediated Rearrangement of Bromohydrins |
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