Improved Synthetic Utility of a Sluggish Electrophile: Reaction of Chlorosulfonyl Isocyanate with Unreactive and Reactive Alkenes
Abstract Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium w...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2015-07, Vol.47 (13), p.1944-1950 |
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| Hauptverfasser: | , , , , , , , , , |
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| Sprache: | eng |
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| container_end_page | 1950 |
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| container_issue | 13 |
| container_start_page | 1944 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 47 |
| creator | Shellhamer, Dale F. Alexander, Kelsey L. Bunting, Summer A. Elwin, Sarah L. Licata, Christine J. Milligan, Jacob C. Robinson, Ryan D. Shipowick, Danielle E. Smith, Lincoln B. Perry, Marc C. |
| description | Abstract
Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium with an intermediate. A unimolecular reaction of the intermediate at a temperature between –15 and 25 °C is more efficient than the bimolecular reaction of the dissociated reagents above room temperature. This finding provides a method for improving the reactions of CSI with unreactive alkenes. |
| doi_str_mv | 10.1055/s-0034-1380553 |
| format | Article |
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Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium with an intermediate. A unimolecular reaction of the intermediate at a temperature between –15 and 25 °C is more efficient than the bimolecular reaction of the dissociated reagents above room temperature. This finding provides a method for improving the reactions of CSI with unreactive alkenes.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0034-1380553</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2015-07, Vol.47 (13), p.1944-1950</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c347t-26a329fd4793c2d30dbe4f9b7aa167334cd65e252068f09daa352bc98d0596e43</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0034-1380553.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0034-1380553$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>315,781,785,3018,3019,27929,27930,54564,54565</link.rule.ids></links><search><creatorcontrib>Shellhamer, Dale F.</creatorcontrib><creatorcontrib>Alexander, Kelsey L.</creatorcontrib><creatorcontrib>Bunting, Summer A.</creatorcontrib><creatorcontrib>Elwin, Sarah L.</creatorcontrib><creatorcontrib>Licata, Christine J.</creatorcontrib><creatorcontrib>Milligan, Jacob C.</creatorcontrib><creatorcontrib>Robinson, Ryan D.</creatorcontrib><creatorcontrib>Shipowick, Danielle E.</creatorcontrib><creatorcontrib>Smith, Lincoln B.</creatorcontrib><creatorcontrib>Perry, Marc C.</creatorcontrib><title>Improved Synthetic Utility of a Sluggish Electrophile: Reaction of Chlorosulfonyl Isocyanate with Unreactive and Reactive Alkenes</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium with an intermediate. A unimolecular reaction of the intermediate at a temperature between –15 and 25 °C is more efficient than the bimolecular reaction of the dissociated reagents above room temperature. This finding provides a method for improving the reactions of CSI with unreactive alkenes.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp1kEtLAzEUhYMoWKtb1_kDqXnMK-6k-CgIgrXgbkiTO53UNCmTtDJL_7lT262ry-F-53A4CN0yOmE0z-8ioVRkhIlqUOIMjVgmSsIZ_TxHo-ElSVlV7BJdxbimlJZcyBH6mW22XdiDwfPepxaS1XiRrLOpx6HBCs_dbrWyscWPDnTqwra1Du7xOyidbPAHaNq60IW4c03wvcOzGHSvvEqAv21q8cJ3f_AesPLm5BzEg_sCD_EaXTTKRbg53TFaPD1-TF_I69vzbPrwSrTIykR4oQSXjclKKTQ3gpolZI1clkqxohQi06bIgeecFlVDpVFK5HypZWVoLgvIxBhNjrl66Bo7aOptZzeq62tG68OAdawPA9anAQcDORpSa2ED9TrsOj80_I__BXMxdBM</recordid><startdate>20150701</startdate><enddate>20150701</enddate><creator>Shellhamer, Dale F.</creator><creator>Alexander, Kelsey L.</creator><creator>Bunting, Summer A.</creator><creator>Elwin, Sarah L.</creator><creator>Licata, Christine J.</creator><creator>Milligan, Jacob C.</creator><creator>Robinson, Ryan D.</creator><creator>Shipowick, Danielle E.</creator><creator>Smith, Lincoln B.</creator><creator>Perry, Marc C.</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150701</creationdate><title>Improved Synthetic Utility of a Sluggish Electrophile: Reaction of Chlorosulfonyl Isocyanate with Unreactive and Reactive Alkenes</title><author>Shellhamer, Dale F. ; Alexander, Kelsey L. ; Bunting, Summer A. ; Elwin, Sarah L. ; Licata, Christine J. ; Milligan, Jacob C. ; Robinson, Ryan D. ; Shipowick, Danielle E. ; Smith, Lincoln B. ; Perry, Marc C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c347t-26a329fd4793c2d30dbe4f9b7aa167334cd65e252068f09daa352bc98d0596e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shellhamer, Dale F.</creatorcontrib><creatorcontrib>Alexander, Kelsey L.</creatorcontrib><creatorcontrib>Bunting, Summer A.</creatorcontrib><creatorcontrib>Elwin, Sarah L.</creatorcontrib><creatorcontrib>Licata, Christine J.</creatorcontrib><creatorcontrib>Milligan, Jacob C.</creatorcontrib><creatorcontrib>Robinson, Ryan D.</creatorcontrib><creatorcontrib>Shipowick, Danielle E.</creatorcontrib><creatorcontrib>Smith, Lincoln B.</creatorcontrib><creatorcontrib>Perry, Marc C.</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shellhamer, Dale F.</au><au>Alexander, Kelsey L.</au><au>Bunting, Summer A.</au><au>Elwin, Sarah L.</au><au>Licata, Christine J.</au><au>Milligan, Jacob C.</au><au>Robinson, Ryan D.</au><au>Shipowick, Danielle E.</au><au>Smith, Lincoln B.</au><au>Perry, Marc C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Improved Synthetic Utility of a Sluggish Electrophile: Reaction of Chlorosulfonyl Isocyanate with Unreactive and Reactive Alkenes</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2015-07-01</date><risdate>2015</risdate><volume>47</volume><issue>13</issue><spage>1944</spage><epage>1950</epage><pages>1944-1950</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between –15 and 25 °C because, at these temperatures, CSI and the alkene are in equilibrium with an intermediate. A unimolecular reaction of the intermediate at a temperature between –15 and 25 °C is more efficient than the bimolecular reaction of the dissociated reagents above room temperature. This finding provides a method for improving the reactions of CSI with unreactive alkenes.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0034-1380553</doi><tpages>7</tpages></addata></record> |
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| title | Improved Synthetic Utility of a Sluggish Electrophile: Reaction of Chlorosulfonyl Isocyanate with Unreactive and Reactive Alkenes |
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