Building Giant Carbocycles by Reversible C−C Bond Formation
We describe a simple way to build giant macrocyclic hydrocarbons by the reversible formation of carbon–carbon bonds. Specifically, extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, giving the largest hydrocarbon that...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-01, Vol.55 (3), p.894-898 |
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| container_end_page | 898 |
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| container_issue | 3 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Beaudoin, Daniel Levasseur-Grenon, Olivier Maris, Thierry Wuest, James D. |
| description | We describe a simple way to build giant macrocyclic hydrocarbons by the reversible formation of carbon–carbon bonds. Specifically, extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, giving the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date.
Giant macrocyclic hydrocarbons can be obtained by a facile approach that is based on the reversible formation of carbon–carbon bonds. Extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, leading to the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date. |
| doi_str_mv | 10.1002/anie.201509608 |
| format | Article |
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Giant macrocyclic hydrocarbons can be obtained by a facile approach that is based on the reversible formation of carbon–carbon bonds. Extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, leading to the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201509608</identifier><identifier>PMID: 26597318</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Bonding ; Buildings ; carbocycles ; Carbon ; Construction specifications ; Crystallization ; Derivatives ; dynamic covalent chemistry ; Hydrocarbons ; macrocycles ; Oligomerization ; radicals ; spirobifluorenes ; X-ray diffraction</subject><ispartof>Angewandte Chemie International Edition, 2016-01, Vol.55 (3), p.894-898</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6128-3e1b2b8ff32301009b326d00b1ab8facd580bbf236c3a5eb2c231ea194e160f53</citedby><cites>FETCH-LOGICAL-c6128-3e1b2b8ff32301009b326d00b1ab8facd580bbf236c3a5eb2c231ea194e160f53</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%2Fanie.201509608$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201509608$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26597318$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Beaudoin, Daniel</creatorcontrib><creatorcontrib>Levasseur-Grenon, Olivier</creatorcontrib><creatorcontrib>Maris, Thierry</creatorcontrib><creatorcontrib>Wuest, James D.</creatorcontrib><title>Building Giant Carbocycles by Reversible C−C Bond Formation</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>We describe a simple way to build giant macrocyclic hydrocarbons by the reversible formation of carbon–carbon bonds. Specifically, extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, giving the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date.
Giant macrocyclic hydrocarbons can be obtained by a facile approach that is based on the reversible formation of carbon–carbon bonds. Extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, leading to the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date.</description><subject>Bonding</subject><subject>Buildings</subject><subject>carbocycles</subject><subject>Carbon</subject><subject>Construction specifications</subject><subject>Crystallization</subject><subject>Derivatives</subject><subject>dynamic covalent chemistry</subject><subject>Hydrocarbons</subject><subject>macrocycles</subject><subject>Oligomerization</subject><subject>radicals</subject><subject>spirobifluorenes</subject><subject>X-ray diffraction</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkEFPFDEUxxuDEVi9ciSTcPEya18f7XQOHmACKwlgFIzGS9POvCHF2Rlsd9D9Bp79iH4SSxY3xAOc-tL83j_v_2NsB_gUOBdvbO9pKjhIXiqun7EtkAJyLArcSPM-Yl5oCZtsO8brxGvN1Qu2KZQsCwS9xd4ejr5rfH-VzbztF1llgxvqZd1RzNwy-0i3FKJ3HWXVn1-_q-xw6JvseAhzu_BD_5I9b20X6dX9O2Gfjo8uq3f56fvZSXVwmtcKhM6RwAmn2xYF8nR26VCohnMHNv3aupGaO9cKVDVaSU7UAoEslPsEircSJ-z1KvcmDN9Higsz97GmrrM9DWM0UKTyqVsqNWF7_6HXwxj6dJ2BkqtkJrl5lCqk1EqjhERNV1QdhhgDteYm-LkNSwPc3Ok3d_rNWn9a2L2PHd2cmjX-z3cCyhXww3e0fCLOHJyfHD0Mz1e7Pi7o53rXhm9GFVhI8_l8Zr5e8C94NjszH_Av5fWeaw</recordid><startdate>20160118</startdate><enddate>20160118</enddate><creator>Beaudoin, Daniel</creator><creator>Levasseur-Grenon, Olivier</creator><creator>Maris, Thierry</creator><creator>Wuest, James D.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160118</creationdate><title>Building Giant Carbocycles by Reversible C−C Bond Formation</title><author>Beaudoin, Daniel ; Levasseur-Grenon, Olivier ; Maris, Thierry ; Wuest, James D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6128-3e1b2b8ff32301009b326d00b1ab8facd580bbf236c3a5eb2c231ea194e160f53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Bonding</topic><topic>Buildings</topic><topic>carbocycles</topic><topic>Carbon</topic><topic>Construction specifications</topic><topic>Crystallization</topic><topic>Derivatives</topic><topic>dynamic covalent chemistry</topic><topic>Hydrocarbons</topic><topic>macrocycles</topic><topic>Oligomerization</topic><topic>radicals</topic><topic>spirobifluorenes</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Beaudoin, Daniel</creatorcontrib><creatorcontrib>Levasseur-Grenon, Olivier</creatorcontrib><creatorcontrib>Maris, Thierry</creatorcontrib><creatorcontrib>Wuest, James D.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Beaudoin, Daniel</au><au>Levasseur-Grenon, Olivier</au><au>Maris, Thierry</au><au>Wuest, James D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Building Giant Carbocycles by Reversible C−C Bond Formation</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-01-18</date><risdate>2016</risdate><volume>55</volume><issue>3</issue><spage>894</spage><epage>898</epage><pages>894-898</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>We describe a simple way to build giant macrocyclic hydrocarbons by the reversible formation of carbon–carbon bonds. Specifically, extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, giving the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date.
Giant macrocyclic hydrocarbons can be obtained by a facile approach that is based on the reversible formation of carbon–carbon bonds. Extended spirobifluorene‐substituted derivatives of Wittig's hydrocarbon were synthesized and found to undergo oligomerization, leading to the largest hydrocarbon that has been crystallized and characterized by X‐ray diffraction to date.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26597318</pmid><doi>10.1002/anie.201509608</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Bonding Buildings carbocycles Carbon Construction specifications Crystallization Derivatives dynamic covalent chemistry Hydrocarbons macrocycles Oligomerization radicals spirobifluorenes X-ray diffraction |
| title | Building Giant Carbocycles by Reversible C−C Bond Formation |
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