Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts
The reactivity of functionalized ynamides and arylynamines with tetracyanoethylene at room temperature was evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes (TCBDs) were obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence....
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2017-06, Vol.12 (12), p.1338-1346 |
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| creator | Betou, Marie Durand, Raphaël J. Sallustrau, Dr Antoine Gousset, Claire Le Coz, Erwann Leroux, Yann R. Toupet, Dr Loïc Trzop, Elzbieta Roisnel, Thierry Trolez, Yann |
| description | The reactivity of functionalized ynamides and arylynamines with tetracyanoethylene at room temperature was evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes (TCBDs) were obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield of the reaction was investigated, in particular concerning multiple ynamides. These TCBDs were characterized by various spectroscopic techniques and electrochemistry and X‐ray diffraction in some cases.
Sequence of events: The reactivity of functionalized ynamides and arylynamines towards tetracyanoethylene at room temperature is evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes are obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield is investigated, in particular concerning multiple ynamides. |
| doi_str_mv | 10.1002/asia.201700353 |
| format | Article |
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Sequence of events: The reactivity of functionalized ynamides and arylynamines towards tetracyanoethylene at room temperature is evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes are obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield is investigated, in particular concerning multiple ynamides.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201700353</identifier><identifier>PMID: 28407369</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Chemical Sciences ; Chemistry ; Cycloaddition ; dienes ; Diffraction ; Electrochemistry ; Functional groups ; Optoelectronics ; Organic chemistry ; Physics ; retro reactions ; Spectroscopy ; X-ray diffraction ; ynamides</subject><ispartof>Chemistry, an Asian journal, 2017-06, Vol.12 (12), p.1338-1346</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4843-ceabd6a390034beccf7e9486783e653878005f7623acfa41bfe71a2c61a2cce33</citedby><cites>FETCH-LOGICAL-c4843-ceabd6a390034beccf7e9486783e653878005f7623acfa41bfe71a2c61a2cce33</cites><orcidid>0000-0002-4816-240X ; 0000-0002-5421-9556 ; 0000-0002-6088-4472 ; 0000-0003-1998-1825 ; 0000-0002-4737-9922</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%2Fasia.201700353$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201700353$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28407369$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://univ-rennes.hal.science/hal-01544243$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Betou, Marie</creatorcontrib><creatorcontrib>Durand, Raphaël J.</creatorcontrib><creatorcontrib>Sallustrau, Dr Antoine</creatorcontrib><creatorcontrib>Gousset, Claire</creatorcontrib><creatorcontrib>Le Coz, Erwann</creatorcontrib><creatorcontrib>Leroux, Yann R.</creatorcontrib><creatorcontrib>Toupet, Dr Loïc</creatorcontrib><creatorcontrib>Trzop, Elzbieta</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Trolez, Yann</creatorcontrib><title>Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts</title><title>Chemistry, an Asian journal</title><addtitle>Chem Asian J</addtitle><description>The reactivity of functionalized ynamides and arylynamines with tetracyanoethylene at room temperature was evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes (TCBDs) were obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield of the reaction was investigated, in particular concerning multiple ynamides. These TCBDs were characterized by various spectroscopic techniques and electrochemistry and X‐ray diffraction in some cases.
Sequence of events: The reactivity of functionalized ynamides and arylynamines towards tetracyanoethylene at room temperature is evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes are obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield is investigated, in particular concerning multiple ynamides.</description><subject>Adducts</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Cycloaddition</subject><subject>dienes</subject><subject>Diffraction</subject><subject>Electrochemistry</subject><subject>Functional groups</subject><subject>Optoelectronics</subject><subject>Organic chemistry</subject><subject>Physics</subject><subject>retro reactions</subject><subject>Spectroscopy</subject><subject>X-ray diffraction</subject><subject>ynamides</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkUtr3DAURk1padKk2y6LoJsUOhO9bMvdmZA0gYGUJoV2Je7I14yCbU0lOcFZ5LdXZtIpdNONXpx7pKsvy94xumSU8lMIFpacspJSkYsX2SFTBVvIkv14uV9zdZC9CeGO0pzTSr3ODriStBRFdZg9fUMw0d7bOBHXkotxSDs3QGcfsSE_B-htg4E82Lghtxg9mAkGh3EzdTjgZ3Jj3BY_kZXtbYS5MhAYGnK9jQ47NNG7wRry1SfKR5tM6ZK4QVI3zWhiOM5etdAFfPs8H2XfL85vzy4Xq-svV2f1amGkkmJhENZNAaJKXco1GtOWWElVlEpgkQtVqtRbWxZcgGlBsnWLJQNuinkwKMRR9nHn3UCnt9724CftwOrLeqXnM8pyKbkU9yyxJzt2692vEUPUvQ0Guw4GdGPQTClVKK7yIqEf_kHv3OjT7yWqYrTkIoGJWu4o410IHtv9CxjVc4p6TlHvU0wF75-147rHZo__iS0B1Q54sB1O_9Hp-uaq_iv_DY1Nqls</recordid><startdate>20170619</startdate><enddate>20170619</enddate><creator>Betou, Marie</creator><creator>Durand, Raphaël J.</creator><creator>Sallustrau, Dr Antoine</creator><creator>Gousset, Claire</creator><creator>Le Coz, Erwann</creator><creator>Leroux, Yann R.</creator><creator>Toupet, Dr Loïc</creator><creator>Trzop, Elzbieta</creator><creator>Roisnel, Thierry</creator><creator>Trolez, Yann</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-4816-240X</orcidid><orcidid>https://orcid.org/0000-0002-5421-9556</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0003-1998-1825</orcidid><orcidid>https://orcid.org/0000-0002-4737-9922</orcidid></search><sort><creationdate>20170619</creationdate><title>Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts</title><author>Betou, Marie ; Durand, Raphaël J. ; Sallustrau, Dr Antoine ; Gousset, Claire ; Le Coz, Erwann ; Leroux, Yann R. ; Toupet, Dr Loïc ; Trzop, Elzbieta ; Roisnel, Thierry ; Trolez, Yann</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4843-ceabd6a390034beccf7e9486783e653878005f7623acfa41bfe71a2c61a2cce33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Adducts</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Cycloaddition</topic><topic>dienes</topic><topic>Diffraction</topic><topic>Electrochemistry</topic><topic>Functional groups</topic><topic>Optoelectronics</topic><topic>Organic chemistry</topic><topic>Physics</topic><topic>retro reactions</topic><topic>Spectroscopy</topic><topic>X-ray diffraction</topic><topic>ynamides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Betou, Marie</creatorcontrib><creatorcontrib>Durand, Raphaël J.</creatorcontrib><creatorcontrib>Sallustrau, Dr Antoine</creatorcontrib><creatorcontrib>Gousset, Claire</creatorcontrib><creatorcontrib>Le Coz, Erwann</creatorcontrib><creatorcontrib>Leroux, Yann R.</creatorcontrib><creatorcontrib>Toupet, Dr Loïc</creatorcontrib><creatorcontrib>Trzop, Elzbieta</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Trolez, Yann</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Betou, Marie</au><au>Durand, Raphaël J.</au><au>Sallustrau, Dr Antoine</au><au>Gousset, Claire</au><au>Le Coz, Erwann</au><au>Leroux, Yann R.</au><au>Toupet, Dr Loïc</au><au>Trzop, Elzbieta</au><au>Roisnel, Thierry</au><au>Trolez, Yann</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem Asian J</addtitle><date>2017-06-19</date><risdate>2017</risdate><volume>12</volume><issue>12</issue><spage>1338</spage><epage>1346</epage><pages>1338-1346</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>The reactivity of functionalized ynamides and arylynamines with tetracyanoethylene at room temperature was evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes (TCBDs) were obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield of the reaction was investigated, in particular concerning multiple ynamides. These TCBDs were characterized by various spectroscopic techniques and electrochemistry and X‐ray diffraction in some cases.
Sequence of events: The reactivity of functionalized ynamides and arylynamines towards tetracyanoethylene at room temperature is evaluated. In most cases, the corresponding 1,1,4,4‐tetracyanobutadienes are obtained in good to excellent yields through a [2+2]‐cycloaddition/[2+2]‐retro‐electrocyclization sequence. The influence of diverse functional groups on the yield is investigated, in particular concerning multiple ynamides.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28407369</pmid><doi>10.1002/asia.201700353</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-4816-240X</orcidid><orcidid>https://orcid.org/0000-0002-5421-9556</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0003-1998-1825</orcidid><orcidid>https://orcid.org/0000-0002-4737-9922</orcidid><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Adducts Chemical Sciences Chemistry Cycloaddition dienes Diffraction Electrochemistry Functional groups Optoelectronics Organic chemistry Physics retro reactions Spectroscopy X-ray diffraction ynamides |
| title | Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts |
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