Reactions of Carbanions of 1-Chloro-5-(phenylsulfonyl)pent-2-enes: Synthesis of Vinyl-Substituted Tetrahydrofurans
The carbanions of (E)‐ and (Z)‐1‐chloro‐5‐(phenylsulfonyl)‐pent‐2‐enes can be considered as vinylogues of γ‐chlorocarbanions. Because in these cases intramolecular 1,3‐substitution by a SN2′ mechanism leading to vinylcyclopropanes is a relatively slow process these carbanions can be efficiently trap...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2009-08, Vol.2009 (22), p.3732-3740 |
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| container_title | European Journal of Organic Chemistry |
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| creator | Wojtasiewicz, Anna Lewandowski, Bartosz Judka, Marek Mąkosza, Mieczysław |
| description | The carbanions of (E)‐ and (Z)‐1‐chloro‐5‐(phenylsulfonyl)‐pent‐2‐enes can be considered as vinylogues of γ‐chlorocarbanions. Because in these cases intramolecular 1,3‐substitution by a SN2′ mechanism leading to vinylcyclopropanes is a relatively slow process these carbanions can be efficiently trapped by active electrophilic reagents such as aldehydes. Subsequent intramolecular SN2′ 1,5‐substitution of the aldol anions produced gives vinyl‐substituted tetrahydrofurans. Thus, an efficient method for the synthesis of 2,3‐disubstituted‐5‐vinyltetrahydrofurans has been elaborated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Carbanions of 1‐chloro‐5‐(phenylsulfonyl)pent‐2‐enes can be considered as vinylogues of γ‐halocarbanions. They undergo intramolecular SN2′ 1,3‐substitution and 1,5‐elimination to produce 2‐(phenylsulfonyl)‐1‐vinylcyclopropanes and 1‐(phenylsulfonyl)penta‐2,4‐dienes. They also add rapidly to aromatic aldehydes to produce the corresponding 2‐aryl‐3‐(phenylsulfonyl)‐5‐vinyltetrahydrofurans. |
| doi_str_mv | 10.1002/ejoc.200900275 |
| format | Article |
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Carbanions of 1‐chloro‐5‐(phenylsulfonyl)pent‐2‐enes can be considered as vinylogues of γ‐halocarbanions. They undergo intramolecular SN2′ 1,3‐substitution and 1,5‐elimination to produce 2‐(phenylsulfonyl)‐1‐vinylcyclopropanes and 1‐(phenylsulfonyl)penta‐2,4‐dienes. They also add rapidly to aromatic aldehydes to produce the corresponding 2‐aryl‐3‐(phenylsulfonyl)‐5‐vinyltetrahydrofurans.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200900275</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Carbanions ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Nucleophilic substitution ; Organic chemistry ; Oxygen heterocycles ; Preparations and properties ; Sulfones</subject><ispartof>European Journal of Organic Chemistry, 2009-08, Vol.2009 (22), p.3732-3740</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3575-5c30ea0de9987799ed8bc60891b8407883eedd40e27e4506cb796324cb5185393</citedby><cites>FETCH-LOGICAL-c3575-5c30ea0de9987799ed8bc60891b8407883eedd40e27e4506cb796324cb5185393</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.200900275$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200900275$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,780,784,792,1417,27922,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21754525$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Wojtasiewicz, Anna</creatorcontrib><creatorcontrib>Lewandowski, Bartosz</creatorcontrib><creatorcontrib>Judka, Marek</creatorcontrib><creatorcontrib>Mąkosza, Mieczysław</creatorcontrib><title>Reactions of Carbanions of 1-Chloro-5-(phenylsulfonyl)pent-2-enes: Synthesis of Vinyl-Substituted Tetrahydrofurans</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The carbanions of (E)‐ and (Z)‐1‐chloro‐5‐(phenylsulfonyl)‐pent‐2‐enes can be considered as vinylogues of γ‐chlorocarbanions. Because in these cases intramolecular 1,3‐substitution by a SN2′ mechanism leading to vinylcyclopropanes is a relatively slow process these carbanions can be efficiently trapped by active electrophilic reagents such as aldehydes. Subsequent intramolecular SN2′ 1,5‐substitution of the aldol anions produced gives vinyl‐substituted tetrahydrofurans. Thus, an efficient method for the synthesis of 2,3‐disubstituted‐5‐vinyltetrahydrofurans has been elaborated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Carbanions of 1‐chloro‐5‐(phenylsulfonyl)pent‐2‐enes can be considered as vinylogues of γ‐halocarbanions. They undergo intramolecular SN2′ 1,3‐substitution and 1,5‐elimination to produce 2‐(phenylsulfonyl)‐1‐vinylcyclopropanes and 1‐(phenylsulfonyl)penta‐2,4‐dienes. They also add rapidly to aromatic aldehydes to produce the corresponding 2‐aryl‐3‐(phenylsulfonyl)‐5‐vinyltetrahydrofurans.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Carbanions</subject><subject>Chemistry</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>Nucleophilic substitution</subject><subject>Organic chemistry</subject><subject>Oxygen heterocycles</subject><subject>Preparations and properties</subject><subject>Sulfones</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAQhSMEEqWwMmdBgsHFjuM4ZkOhtEBFpbbQbpbjXJSUkER2Ksi_J6VQsTG9O9377k7Pcc4JHhCMvWtYV3rgYSy6hrMDp0ewEAgHAh92tU99RARdHTsn1q5xZwsC0nPMDJRu8qq0bpW6kTKxKn87gqKsqEyFGLqsMyjbwm6KtOr0qoayQR6CEuyNO2_LJgObf0OveTdH801sm7zZNJC4C2iMytrEVOnGqNKeOkepKiyc_WjfebkfLqIxmkxHD9HtBGnKOENMUwwKJyBEyLkQkISxDnAoSBz6mIchBUgSH4PHwWc40DEXAfV8HTMSMipo3xns9mpTWWsglbXJ35VpJcFym5jcJib3iXXAxQ6oldWqSLtndW73lEc485m39Ymd7yMvoP1nqxw-TqO_N9COzW0Dn3tWmTcZcNrZl88juRo_-Xx2t5Qr-gXxq403</recordid><startdate>200908</startdate><enddate>200908</enddate><creator>Wojtasiewicz, Anna</creator><creator>Lewandowski, Bartosz</creator><creator>Judka, Marek</creator><creator>Mąkosza, Mieczysław</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>200908</creationdate><title>Reactions of Carbanions of 1-Chloro-5-(phenylsulfonyl)pent-2-enes: Synthesis of Vinyl-Substituted Tetrahydrofurans</title><author>Wojtasiewicz, Anna ; Lewandowski, Bartosz ; Judka, Marek ; Mąkosza, Mieczysław</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3575-5c30ea0de9987799ed8bc60891b8407883eedd40e27e4506cb796324cb5185393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Carbanions</topic><topic>Chemistry</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>Nucleophilic substitution</topic><topic>Organic chemistry</topic><topic>Oxygen heterocycles</topic><topic>Preparations and properties</topic><topic>Sulfones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wojtasiewicz, Anna</creatorcontrib><creatorcontrib>Lewandowski, Bartosz</creatorcontrib><creatorcontrib>Judka, Marek</creatorcontrib><creatorcontrib>Mąkosza, Mieczysław</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>Wojtasiewicz, Anna</au><au>Lewandowski, Bartosz</au><au>Judka, Marek</au><au>Mąkosza, Mieczysław</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactions of Carbanions of 1-Chloro-5-(phenylsulfonyl)pent-2-enes: Synthesis of Vinyl-Substituted Tetrahydrofurans</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2009-08</date><risdate>2009</risdate><volume>2009</volume><issue>22</issue><spage>3732</spage><epage>3740</epage><pages>3732-3740</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The carbanions of (E)‐ and (Z)‐1‐chloro‐5‐(phenylsulfonyl)‐pent‐2‐enes can be considered as vinylogues of γ‐chlorocarbanions. Because in these cases intramolecular 1,3‐substitution by a SN2′ mechanism leading to vinylcyclopropanes is a relatively slow process these carbanions can be efficiently trapped by active electrophilic reagents such as aldehydes. Subsequent intramolecular SN2′ 1,5‐substitution of the aldol anions produced gives vinyl‐substituted tetrahydrofurans. Thus, an efficient method for the synthesis of 2,3‐disubstituted‐5‐vinyltetrahydrofurans has been elaborated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Carbanions of 1‐chloro‐5‐(phenylsulfonyl)pent‐2‐enes can be considered as vinylogues of γ‐halocarbanions. They undergo intramolecular SN2′ 1,3‐substitution and 1,5‐elimination to produce 2‐(phenylsulfonyl)‐1‐vinylcyclopropanes and 1‐(phenylsulfonyl)penta‐2,4‐dienes. They also add rapidly to aromatic aldehydes to produce the corresponding 2‐aryl‐3‐(phenylsulfonyl)‐5‐vinyltetrahydrofurans.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200900275</doi><tpages>9</tpages></addata></record> |
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| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Carbanions Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Nucleophilic substitution Organic chemistry Oxygen heterocycles Preparations and properties Sulfones |
| title | Reactions of Carbanions of 1-Chloro-5-(phenylsulfonyl)pent-2-enes: Synthesis of Vinyl-Substituted Tetrahydrofurans |
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