Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case
Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2011-05, Vol.2011 (13), p.2548-2553 |
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| container_issue | 13 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2011 |
| creator | Eger, Wilhelm A. Grange, Rebecca L. Schill, Heiko Goumont, Régis Clark, Timothy Williams, Craig M. |
| description | Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
Acyl anion equivalents are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. This investigation evaluates the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far fromsuperior, reactivity of TosMIC is presented. |
| doi_str_mv | 10.1002/ejoc.201001680 |
| format | Article |
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Acyl anion equivalents are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. This investigation evaluates the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far fromsuperior, reactivity of TosMIC is presented.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201001680</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Acyl anion equivalent ; Carbonyl equivalent ; Chemical reactivity ; Chemistry ; Epoxides ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Reactivity and mechanisms ; Umpolung</subject><ispartof>European Journal of Organic Chemistry, 2011-05, Vol.2011 (13), p.2548-2553</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3570-ded05dec88a39b4c8c5b566858921e429f63d8d151764185beea30af8fef2cdc3</citedby><cites>FETCH-LOGICAL-c3570-ded05dec88a39b4c8c5b566858921e429f63d8d151764185beea30af8fef2cdc3</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%2Fejoc.201001680$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201001680$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,780,784,792,1416,27921,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24134212$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Eger, Wilhelm A.</creatorcontrib><creatorcontrib>Grange, Rebecca L.</creatorcontrib><creatorcontrib>Schill, Heiko</creatorcontrib><creatorcontrib>Goumont, Régis</creatorcontrib><creatorcontrib>Clark, Timothy</creatorcontrib><creatorcontrib>Williams, Craig M.</creatorcontrib><title>Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
Acyl anion equivalents are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. This investigation evaluates the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far fromsuperior, reactivity of TosMIC is presented.</description><subject>Acyl anion equivalent</subject><subject>Carbonyl equivalent</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Epoxides</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Umpolung</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAUhCMEEqWwMmdhTLHj2LHZqlAKVaESagVisVz7BVxCEuJQmn9PoqCKjeluuO9OOs87x2iEEQovYVPoUYhajxlHB94AIyECxAQ6bH1EogAL8nzsnTi3QQgJxvDAW61yA5WrVW5s_urXb-A_gtK13dq68YvUH-sm88e5LXJ_8vlltyqDvHZX_rJNTspiZ01LdOiihLzTRDk49Y5SlTk4-9Wht7qZLJPbYL6Y3iXjeaAJjVFgwCBqQHOuiFhHmmu6poxxykWIIQpFyojhBlMcswhzugZQBKmUp5CG2mgy9EZ9r64K5ypIZVnZD1U1EiPZnSK7U-T-lBa46IFSOa2ytFK5tm5PhREmUYjDNif63LfNoPmnVU5mi-TvRtCz1tWw27OqepcsJjGVTw9T-bKcUTFPruU9-QH8o4LB</recordid><startdate>201105</startdate><enddate>201105</enddate><creator>Eger, Wilhelm A.</creator><creator>Grange, Rebecca L.</creator><creator>Schill, Heiko</creator><creator>Goumont, Régis</creator><creator>Clark, Timothy</creator><creator>Williams, Craig M.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201105</creationdate><title>Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case</title><author>Eger, Wilhelm A. ; Grange, Rebecca L. ; Schill, Heiko ; Goumont, Régis ; Clark, Timothy ; Williams, Craig M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3570-ded05dec88a39b4c8c5b566858921e429f63d8d151764185beea30af8fef2cdc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Acyl anion equivalent</topic><topic>Carbonyl equivalent</topic><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Epoxides</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Umpolung</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eger, Wilhelm A.</creatorcontrib><creatorcontrib>Grange, Rebecca L.</creatorcontrib><creatorcontrib>Schill, Heiko</creatorcontrib><creatorcontrib>Goumont, Régis</creatorcontrib><creatorcontrib>Clark, Timothy</creatorcontrib><creatorcontrib>Williams, Craig M.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eger, Wilhelm A.</au><au>Grange, Rebecca L.</au><au>Schill, Heiko</au><au>Goumont, Régis</au><au>Clark, Timothy</au><au>Williams, Craig M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2011-05</date><risdate>2011</risdate><volume>2011</volume><issue>13</issue><spage>2548</spage><epage>2553</epage><pages>2548-2553</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
Acyl anion equivalents are the practitioner's first choice en route to 1,3‐hydroxy keto compounds from epoxides. This investigation evaluates the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far fromsuperior, reactivity of TosMIC is presented.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201001680</doi><tpages>6</tpages></addata></record> |
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| ispartof | European Journal of Organic Chemistry, 2011-05, Vol.2011 (13), p.2548-2553 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_201001680 |
| source | Wiley Online Library All Journals |
| subjects | Acyl anion equivalent Carbonyl equivalent Chemical reactivity Chemistry Epoxides Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties Reactivity and mechanisms Umpolung |
| title | Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case |
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