A Facile Preparation of N‐Heterocyclic Olefins: Ring‐Opening Polymerization of β‐Butyrolactone and Frustrated Lewis Pair Reactivity
A direct synthesis of N‐heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N‐heterocyclic carbenes and N‐aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π‐extended analogues. The prepared NHOs initiated the ring‐opening polymerization of β‐b...
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| Veröffentlicht in: | Chemistry : a European journal 2024-02, Vol.30 (8), p.e202303358-n/a |
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| creator | Rajendran, Natesan Mannangatti Lu, Qi Bouffard, Jean |
| description | A direct synthesis of N‐heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N‐heterocyclic carbenes and N‐aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π‐extended analogues. The prepared NHOs initiated the ring‐opening polymerization of β‐butyrolactone, and insertion of aldehyde and nitrile into an NHO‐B(C6F5)3 adduct was demonstrated.
Diverse N‐heterocyclic olefins (NHOs) were prepared by the direct reaction of NHCs or MICs with N‐aziridinylimines. The prepared NHOs’ activity in ring‐opening polymerizations and their frustrated Lewis pair reactivity were studied. |
| doi_str_mv | 10.1002/chem.202303358 |
| format | Article |
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Diverse N‐heterocyclic olefins (NHOs) were prepared by the direct reaction of NHCs or MICs with N‐aziridinylimines. The prepared NHOs’ activity in ring‐opening polymerizations and their frustrated Lewis pair reactivity were studied.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202303358</identifier><identifier>PMID: 38109087</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Alkenes ; Butyrolactone ; Congeners ; frustrated Lewis pairs ; N-aziridinylimine ; N-heterocyclic carbenes ; N-Heterocyclic olefins ; Polymerization ; Ring opening polymerization</subject><ispartof>Chemistry : a European journal, 2024-02, Vol.30 (8), p.e202303358-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2023 Wiley-VCH GmbH.</rights><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3738-efecd3a8a8fd8e398a8fabb6fe5447e2432d9c7185f331734e52e416ec93076a3</citedby><cites>FETCH-LOGICAL-c3738-efecd3a8a8fd8e398a8fabb6fe5447e2432d9c7185f331734e52e416ec93076a3</cites><orcidid>0009-0007-8001-8997 ; 0000-0003-2281-2088 ; 0000-0002-8205-9094</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%2Fchem.202303358$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202303358$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38109087$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rajendran, Natesan Mannangatti</creatorcontrib><creatorcontrib>Lu, Qi</creatorcontrib><creatorcontrib>Bouffard, Jean</creatorcontrib><title>A Facile Preparation of N‐Heterocyclic Olefins: Ring‐Opening Polymerization of β‐Butyrolactone and Frustrated Lewis Pair Reactivity</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A direct synthesis of N‐heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N‐heterocyclic carbenes and N‐aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π‐extended analogues. The prepared NHOs initiated the ring‐opening polymerization of β‐butyrolactone, and insertion of aldehyde and nitrile into an NHO‐B(C6F5)3 adduct was demonstrated.
Diverse N‐heterocyclic olefins (NHOs) were prepared by the direct reaction of NHCs or MICs with N‐aziridinylimines. The prepared NHOs’ activity in ring‐opening polymerizations and their frustrated Lewis pair reactivity were studied.</description><subject>Aldehydes</subject><subject>Alkenes</subject><subject>Butyrolactone</subject><subject>Congeners</subject><subject>frustrated Lewis pairs</subject><subject>N-aziridinylimine</subject><subject>N-heterocyclic carbenes</subject><subject>N-Heterocyclic olefins</subject><subject>Polymerization</subject><subject>Ring opening polymerization</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkcGO0zAQhi0EYsvClSOyxIVLiu1JYpvbUm0pUqHVCs6R60zAqyQudsIqnDhz4ll4EB6CJ8FVlyJx4eSR5pvfo_kIeczZnDMmntuP2M0FE8AACnWHzHgheAayLO6SGdO5zMoC9Bl5EOM1Y0yXAPfJGSjONFNyRr5d0KWxrkW6Dbg3wQzO99Q39O2vr99XOGDwdrKts3TTYuP6-IJeuf5Dam722KeKbn07dRjcl9Pozx-p_XIcpuBbYwffIzV9TZdhjEP6AGu6xhsX6da4QK8wIe6zG6aH5F5j2oiPbt9z8n55-W6xytabV68XF-vMggSVYYO2BqOMamqFoA-F2e3KBos8lyhyELW2kquiAeASciwE5rxEq4HJ0sA5eXbM3Qf_acQ4VJ2LFtvW9OjHWAmdbilyzlRCn_6DXvsx9Gm7RAngRTqpTNT8SNngYwzYVPvgOhOmirPqYKk6WKpOltLAk9vYcddhfcL_aEmAPgI3ycz0n7hqsbp88zf8N1rCo4c</recordid><startdate>20240207</startdate><enddate>20240207</enddate><creator>Rajendran, Natesan Mannangatti</creator><creator>Lu, Qi</creator><creator>Bouffard, Jean</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0009-0007-8001-8997</orcidid><orcidid>https://orcid.org/0000-0003-2281-2088</orcidid><orcidid>https://orcid.org/0000-0002-8205-9094</orcidid></search><sort><creationdate>20240207</creationdate><title>A Facile Preparation of N‐Heterocyclic Olefins: Ring‐Opening Polymerization of β‐Butyrolactone and Frustrated Lewis Pair Reactivity</title><author>Rajendran, Natesan Mannangatti ; Lu, Qi ; Bouffard, Jean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3738-efecd3a8a8fd8e398a8fabb6fe5447e2432d9c7185f331734e52e416ec93076a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aldehydes</topic><topic>Alkenes</topic><topic>Butyrolactone</topic><topic>Congeners</topic><topic>frustrated Lewis pairs</topic><topic>N-aziridinylimine</topic><topic>N-heterocyclic carbenes</topic><topic>N-Heterocyclic olefins</topic><topic>Polymerization</topic><topic>Ring opening polymerization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rajendran, Natesan Mannangatti</creatorcontrib><creatorcontrib>Lu, Qi</creatorcontrib><creatorcontrib>Bouffard, Jean</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rajendran, Natesan Mannangatti</au><au>Lu, Qi</au><au>Bouffard, Jean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Facile Preparation of N‐Heterocyclic Olefins: Ring‐Opening Polymerization of β‐Butyrolactone and Frustrated Lewis Pair Reactivity</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2024-02-07</date><risdate>2024</risdate><volume>30</volume><issue>8</issue><spage>e202303358</spage><epage>n/a</epage><pages>e202303358-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A direct synthesis of N‐heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N‐heterocyclic carbenes and N‐aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π‐extended analogues. The prepared NHOs initiated the ring‐opening polymerization of β‐butyrolactone, and insertion of aldehyde and nitrile into an NHO‐B(C6F5)3 adduct was demonstrated.
Diverse N‐heterocyclic olefins (NHOs) were prepared by the direct reaction of NHCs or MICs with N‐aziridinylimines. The prepared NHOs’ activity in ring‐opening polymerizations and their frustrated Lewis pair reactivity were studied.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>38109087</pmid><doi>10.1002/chem.202303358</doi><tpages>5</tpages><orcidid>https://orcid.org/0009-0007-8001-8997</orcidid><orcidid>https://orcid.org/0000-0003-2281-2088</orcidid><orcidid>https://orcid.org/0000-0002-8205-9094</orcidid></addata></record> |
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| language | eng |
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| subjects | Aldehydes Alkenes Butyrolactone Congeners frustrated Lewis pairs N-aziridinylimine N-heterocyclic carbenes N-Heterocyclic olefins Polymerization Ring opening polymerization |
| title | A Facile Preparation of N‐Heterocyclic Olefins: Ring‐Opening Polymerization of β‐Butyrolactone and Frustrated Lewis Pair Reactivity |
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