Reversible Reactions of Ethylene with Distannynes Under Ambient Conditions
Ethylene's cycloadditions to unsaturated hydrocarbons occupy well-established ground in classical organic chemistry. In contrast, its reactivity toward alkene and alkyne analogs of carbon's heavier-element congeners silicon, germanium, tin, or lead has been little explored. We show here th...
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| Veröffentlicht in: | Science (American Association for the Advancement of Science) 2009-09, Vol.325 (5948), p.1668-1670 |
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| creator | Peng, Yang Ellis, Bobby D Wang, Xinping Fettinger, James C Power, Philip P |
| description | Ethylene's cycloadditions to unsaturated hydrocarbons occupy well-established ground in classical organic chemistry. In contrast, its reactivity toward alkene and alkyne analogs of carbon's heavier-element congeners silicon, germanium, tin, or lead has been little explored. We show here that treatment of the distannynes AriPr⁴SnSnAriPr⁴ [AriPr⁴ = C₆H₃-2,6(C₆H₃-2,6-iPr₂)₂, 1] or AriPr⁸SnSnAriPr⁸ [AriPr⁸ = C₆H-2,6(C₆H₂-2,4,6-iPr₃)₂-3,5-iPr₂, 2] with ethylene under ambient conditions affords the cycloadducts [Formula: see text] (3) or [Formula: see text] (4) that were structurally and spectroscopically characterized. Ethylene incorporation in 3 and 4 involves tin-carbon σ bonding and is shown to be fully reversible under ambient conditions; hydrocarbon solutions of 3 or 4 revert to the distannynes 1 or 2 with ethylene elimination under reduced pressure or upon standing at approximately 25°C. Variable-temperature proton nuclear magnetic resonance studies showed that the enthalpies of reaction were near -48 (3) and -27 (4) kilojoules per mole. |
| doi_str_mv | 10.1126/science.1176443 |
| format | Article |
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In contrast, its reactivity toward alkene and alkyne analogs of carbon's heavier-element congeners silicon, germanium, tin, or lead has been little explored. We show here that treatment of the distannynes AriPr⁴SnSnAriPr⁴ [AriPr⁴ = C₆H₃-2,6(C₆H₃-2,6-iPr₂)₂, 1] or AriPr⁸SnSnAriPr⁸ [AriPr⁸ = C₆H-2,6(C₆H₂-2,4,6-iPr₃)₂-3,5-iPr₂, 2] with ethylene under ambient conditions affords the cycloadducts [Formula: see text] (3) or [Formula: see text] (4) that were structurally and spectroscopically characterized. Ethylene incorporation in 3 and 4 involves tin-carbon σ bonding and is shown to be fully reversible under ambient conditions; hydrocarbon solutions of 3 or 4 revert to the distannynes 1 or 2 with ethylene elimination under reduced pressure or upon standing at approximately 25°C. Variable-temperature proton nuclear magnetic resonance studies showed that the enthalpies of reaction were near -48 (3) and -27 (4) kilojoules per mole.</description><identifier>ISSN: 0036-8075</identifier><identifier>EISSN: 1095-9203</identifier><identifier>DOI: 10.1126/science.1176443</identifier><identifier>PMID: 19779193</identifier><identifier>CODEN: SCIEAS</identifier><language>eng</language><publisher>United States: American Association for the Advancement of Science</publisher><subject>Alkenes ; Alkynes ; Atoms ; Carbon ; Chemical bonding ; Chemical bonds ; Chemical reactions ; Cycloaddition ; Ethylene ; Geometry ; Hydrocarbons ; Molecules ; Organic chemistry ; Tin</subject><ispartof>Science (American Association for the Advancement of Science), 2009-09, Vol.325 (5948), p.1668-1670</ispartof><rights>Copyright 2009 American Association for the Advancement of Science</rights><rights>Copyright © 2009, American Association for the Advancement of Science</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c430t-ef55019e4c53dc2fea825fc9ae3d455fe8e701bdee93e0bfb2708f61352b76033</citedby><cites>FETCH-LOGICAL-c430t-ef55019e4c53dc2fea825fc9ae3d455fe8e701bdee93e0bfb2708f61352b76033</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/40301880$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/40301880$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>314,780,784,803,2884,2885,27924,27925,58017,58250</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19779193$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Peng, Yang</creatorcontrib><creatorcontrib>Ellis, Bobby D</creatorcontrib><creatorcontrib>Wang, Xinping</creatorcontrib><creatorcontrib>Fettinger, James C</creatorcontrib><creatorcontrib>Power, Philip P</creatorcontrib><title>Reversible Reactions of Ethylene with Distannynes Under Ambient Conditions</title><title>Science (American Association for the Advancement of Science)</title><addtitle>Science</addtitle><description>Ethylene's cycloadditions to unsaturated hydrocarbons occupy well-established ground in classical organic chemistry. In contrast, its reactivity toward alkene and alkyne analogs of carbon's heavier-element congeners silicon, germanium, tin, or lead has been little explored. We show here that treatment of the distannynes AriPr⁴SnSnAriPr⁴ [AriPr⁴ = C₆H₃-2,6(C₆H₃-2,6-iPr₂)₂, 1] or AriPr⁸SnSnAriPr⁸ [AriPr⁸ = C₆H-2,6(C₆H₂-2,4,6-iPr₃)₂-3,5-iPr₂, 2] with ethylene under ambient conditions affords the cycloadducts [Formula: see text] (3) or [Formula: see text] (4) that were structurally and spectroscopically characterized. Ethylene incorporation in 3 and 4 involves tin-carbon σ bonding and is shown to be fully reversible under ambient conditions; hydrocarbon solutions of 3 or 4 revert to the distannynes 1 or 2 with ethylene elimination under reduced pressure or upon standing at approximately 25°C. Variable-temperature proton nuclear magnetic resonance studies showed that the enthalpies of reaction were near -48 (3) and -27 (4) kilojoules per mole.</description><subject>Alkenes</subject><subject>Alkynes</subject><subject>Atoms</subject><subject>Carbon</subject><subject>Chemical bonding</subject><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Cycloaddition</subject><subject>Ethylene</subject><subject>Geometry</subject><subject>Hydrocarbons</subject><subject>Molecules</subject><subject>Organic chemistry</subject><subject>Tin</subject><issn>0036-8075</issn><issn>1095-9203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkctvFDEMhyMEokvhzAkYceA2rZ1MXsdqKY-qElJhz9E8HDqr2aQks0X73xPYEZW4cLKi77Mt58fYS4QzRK7Ocz9S6Kk8tGoa8YitEKysLQfxmK0AhKoNaHnCnuW8BSjMiqfsBK3WFq1YsasbuqeUx26i6obafh5jyFX01eV8e5goUPVznG-r92Oe2xAOgXK1CQOl6mLXldVztY5hGP90PWdPfDtlerHUU7b5cPlt_am-_vLx8_riuu4bAXNNXkpAS00vxdBzT63h0ve2JTE0UnoypAG7gcgKgs53XIPxCoXknVYgxCl7d5x7l-KPPeXZ7cbc0zS1geI-O6WVslab_4qisRxRNEV8-4-4jfsUyhGOo1Ao0WCRzo9Sn2LOiby7S-OuTQeH4H6H4ZYw3BJG6Xi9jN13Oxoe_OX3i_DqKGzzHNNf3oAANAYKf3Pkvo2u_Z7G7DZfOWDByjTcSPELW46ZFw</recordid><startdate>20090925</startdate><enddate>20090925</enddate><creator>Peng, Yang</creator><creator>Ellis, Bobby D</creator><creator>Wang, Xinping</creator><creator>Fettinger, James C</creator><creator>Power, Philip P</creator><general>American Association for the Advancement of Science</general><general>The American Association for the Advancement of Science</general><scope>FBQ</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QG</scope><scope>7QL</scope><scope>7QP</scope><scope>7QQ</scope><scope>7QR</scope><scope>7SC</scope><scope>7SE</scope><scope>7SN</scope><scope>7SP</scope><scope>7SR</scope><scope>7SS</scope><scope>7T7</scope><scope>7TA</scope><scope>7TB</scope><scope>7TK</scope><scope>7TM</scope><scope>7U5</scope><scope>7U9</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H94</scope><scope>JG9</scope><scope>JQ2</scope><scope>K9.</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>M7N</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>20090925</creationdate><title>Reversible Reactions of Ethylene with Distannynes Under Ambient Conditions</title><author>Peng, Yang ; Ellis, Bobby D ; Wang, Xinping ; Fettinger, James C ; Power, Philip P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c430t-ef55019e4c53dc2fea825fc9ae3d455fe8e701bdee93e0bfb2708f61352b76033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkenes</topic><topic>Alkynes</topic><topic>Atoms</topic><topic>Carbon</topic><topic>Chemical bonding</topic><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Cycloaddition</topic><topic>Ethylene</topic><topic>Geometry</topic><topic>Hydrocarbons</topic><topic>Molecules</topic><topic>Organic chemistry</topic><topic>Tin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peng, Yang</creatorcontrib><creatorcontrib>Ellis, Bobby D</creatorcontrib><creatorcontrib>Wang, Xinping</creatorcontrib><creatorcontrib>Fettinger, James C</creatorcontrib><creatorcontrib>Power, Philip P</creatorcontrib><collection>AGRIS</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Animal Behavior Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Ecology Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Science (American Association for the Advancement of Science)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peng, Yang</au><au>Ellis, Bobby D</au><au>Wang, Xinping</au><au>Fettinger, James C</au><au>Power, Philip P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reversible Reactions of Ethylene with Distannynes Under Ambient Conditions</atitle><jtitle>Science (American Association for the Advancement of Science)</jtitle><addtitle>Science</addtitle><date>2009-09-25</date><risdate>2009</risdate><volume>325</volume><issue>5948</issue><spage>1668</spage><epage>1670</epage><pages>1668-1670</pages><issn>0036-8075</issn><eissn>1095-9203</eissn><coden>SCIEAS</coden><abstract>Ethylene's cycloadditions to unsaturated hydrocarbons occupy well-established ground in classical organic chemistry. In contrast, its reactivity toward alkene and alkyne analogs of carbon's heavier-element congeners silicon, germanium, tin, or lead has been little explored. We show here that treatment of the distannynes AriPr⁴SnSnAriPr⁴ [AriPr⁴ = C₆H₃-2,6(C₆H₃-2,6-iPr₂)₂, 1] or AriPr⁸SnSnAriPr⁸ [AriPr⁸ = C₆H-2,6(C₆H₂-2,4,6-iPr₃)₂-3,5-iPr₂, 2] with ethylene under ambient conditions affords the cycloadducts [Formula: see text] (3) or [Formula: see text] (4) that were structurally and spectroscopically characterized. Ethylene incorporation in 3 and 4 involves tin-carbon σ bonding and is shown to be fully reversible under ambient conditions; hydrocarbon solutions of 3 or 4 revert to the distannynes 1 or 2 with ethylene elimination under reduced pressure or upon standing at approximately 25°C. Variable-temperature proton nuclear magnetic resonance studies showed that the enthalpies of reaction were near -48 (3) and -27 (4) kilojoules per mole.</abstract><cop>United States</cop><pub>American Association for the Advancement of Science</pub><pmid>19779193</pmid><doi>10.1126/science.1176443</doi><tpages>3</tpages></addata></record> |
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| subjects | Alkenes Alkynes Atoms Carbon Chemical bonding Chemical bonds Chemical reactions Cycloaddition Ethylene Geometry Hydrocarbons Molecules Organic chemistry Tin |
| title | Reversible Reactions of Ethylene with Distannynes Under Ambient Conditions |
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