Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene
New insights into the process of high‐temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characte...
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| Veröffentlicht in: | European journal of organic chemistry 2018-08, Vol.2018 (31), p.4233-4245 |
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| container_title | European journal of organic chemistry |
| container_volume | 2018 |
| creator | Kuvychko, Igor V. Clikeman, Tyler Dubceac, Cristina Chen, Yu‐Sheng Petrukhina, Marina A. Strauss, Steven H. Popov, Alexey A. Boltalina, Olga V. |
| description | New insights into the process of high‐temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron‐deficient PAHs.
Finding the balance between cost and benefit: Drastic energy increase when CF3 groups add to peri‐ and ortho positions on the corannulene rim explains the observed relative distribution of corannulene(CF3)n products in high‐temperature radical trifluoromethylation reactions. |
| doi_str_mv | 10.1002/ejoc.201800508 |
| format | Article |
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Finding the balance between cost and benefit: Drastic energy increase when CF3 groups add to peri‐ and ortho positions on the corannulene rim explains the observed relative distribution of corannulene(CF3)n products in high‐temperature radical trifluoromethylation reactions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201800508</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Corannulene ; DFT calculations ; Fluorinated compounds ; Molecular structure ; Organic chemistry ; Polycyclic aromatic hydrocarbons ; Reagents ; Thermal stability ; Trifluoromethylation</subject><ispartof>European journal of organic chemistry, 2018-08, Vol.2018 (31), p.4233-4245</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0001-7636-2671 ; 0000-0002-7596-0378 ; 0000-0001-7221-1243 ; 0000-0002-7646-7761 ; 0000-0002-8208-3158 ; 0000-0003-0221-7900 ; 0000-0002-6773-2869 ; 0000000176362671 ; 0000000282083158 ; 0000000276467761 ; 0000000172211243 ; 0000000267732869 ; 0000000302217900 ; 0000000275960378</orcidid></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.201800508$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201800508$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.osti.gov/biblio/1491894$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Kuvychko, Igor V.</creatorcontrib><creatorcontrib>Clikeman, Tyler</creatorcontrib><creatorcontrib>Dubceac, Cristina</creatorcontrib><creatorcontrib>Chen, Yu‐Sheng</creatorcontrib><creatorcontrib>Petrukhina, Marina A.</creatorcontrib><creatorcontrib>Strauss, Steven H.</creatorcontrib><creatorcontrib>Popov, Alexey A.</creatorcontrib><creatorcontrib>Boltalina, Olga V.</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><title>Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene</title><title>European journal of organic chemistry</title><description>New insights into the process of high‐temperature trifluoromethylation of polycyclic aromatic hydrocarbons (PAHs) were gained in a detailed study of the reactions between corannulene (C20H10) and CF3I gas. Ten new poly(trifluoromethyl)corannulenes were made in these reactions and were fully characterized. A detailed computational study explains the observed trends in the product distribution and why some products cannot be prepared even with an excess of the reagent gas. The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron‐deficient PAHs.
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(ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><collection>OSTI.GOV</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuvychko, Igor V.</au><au>Clikeman, Tyler</au><au>Dubceac, Cristina</au><au>Chen, Yu‐Sheng</au><au>Petrukhina, Marina A.</au><au>Strauss, Steven H.</au><au>Popov, Alexey A.</au><au>Boltalina, Olga V.</au><aucorp>Argonne National Lab. (ANL), Argonne, IL (United States). 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The approach utilized here may have good predictive value for designing new effective and selective synthetic methodologies for various thermally stable electron‐deficient PAHs.
Finding the balance between cost and benefit: Drastic energy increase when CF3 groups add to peri‐ and ortho positions on the corannulene rim explains the observed relative distribution of corannulene(CF3)n products in high‐temperature radical trifluoromethylation reactions.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201800508</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0001-7636-2671</orcidid><orcidid>https://orcid.org/0000-0002-7596-0378</orcidid><orcidid>https://orcid.org/0000-0001-7221-1243</orcidid><orcidid>https://orcid.org/0000-0002-7646-7761</orcidid><orcidid>https://orcid.org/0000-0002-8208-3158</orcidid><orcidid>https://orcid.org/0000-0003-0221-7900</orcidid><orcidid>https://orcid.org/0000-0002-6773-2869</orcidid><orcidid>https://orcid.org/0000000176362671</orcidid><orcidid>https://orcid.org/0000000282083158</orcidid><orcidid>https://orcid.org/0000000276467761</orcidid><orcidid>https://orcid.org/0000000172211243</orcidid><orcidid>https://orcid.org/0000000267732869</orcidid><orcidid>https://orcid.org/0000000302217900</orcidid><orcidid>https://orcid.org/0000000275960378</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Corannulene DFT calculations Fluorinated compounds Molecular structure Organic chemistry Polycyclic aromatic hydrocarbons Reagents Thermal stability Trifluoromethylation |
| title | Understanding Polyarene Trifluoromethylation with Hot CF3 Radicals Using Corannulene |
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