Ring splitting of azetidin-2-ones via radical anions
The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. Th...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2012-10, Vol.10 (39), p.7928-7932 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7932 |
|---|---|
| container_issue | 39 |
| container_start_page | 7928 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 10 |
| creator | Pérez-Ruiz, Raúl Sáez, Jose A Domingo, Luis R Jiménez, M Consuelo Miranda, Miguel A |
| description | The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry. |
| doi_str_mv | 10.1039/c2ob26528a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1069207331</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1069207331</sourcerecordid><originalsourceid>FETCH-LOGICAL-c287t-36f0efcffa7da185bc0e2566657df8d3b2a811d7a60c981d37676de754169f463</originalsourceid><addsrcrecordid>eNpFkMtKw0AYRgdRbK1ufADJUoTRuWUuSyneoCCIrsOfuchIkqmZRNCnN6W1rr5vcTiLg9A5JdeUcHNjWaqZLJmGAzSnQilMSm4O95-RGTrJ-YMQapQUx2jGmOGEczFH4iV270VeN3EYNi-FAn78EF3sMMOp87n4ilD04KKFpoAupi6foqMATfZnu12gt_u71-UjXj0_PC1vV9gyrQbMZSA-2BBAOaC6rC3xrJRSlsoF7XjNQFPqFEhijaaOK6mk86oUVJogJF-gy6133afP0eehamO2vmmg82nMFSXSMKI4pxN6tUVtn3LufajWfWyh_56galOp-q80wRc771i33u3Rvyz8F34dYS8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1069207331</pqid></control><display><type>article</type><title>Ring splitting of azetidin-2-ones via radical anions</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Pérez-Ruiz, Raúl ; Sáez, Jose A ; Domingo, Luis R ; Jiménez, M Consuelo ; Miranda, Miguel A</creator><creatorcontrib>Pérez-Ruiz, Raúl ; Sáez, Jose A ; Domingo, Luis R ; Jiménez, M Consuelo ; Miranda, Miguel A</creatorcontrib><description>The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c2ob26528a</identifier><identifier>PMID: 22930334</identifier><language>eng</language><publisher>England</publisher><subject>Anions - chemistry ; Azetidines - chemical synthesis ; Azetidines - chemistry ; Free Radicals - chemistry ; Molecular Structure ; Quantum Theory ; Ultraviolet Rays</subject><ispartof>Organic & biomolecular chemistry, 2012-10, Vol.10 (39), p.7928-7932</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c287t-36f0efcffa7da185bc0e2566657df8d3b2a811d7a60c981d37676de754169f463</citedby><cites>FETCH-LOGICAL-c287t-36f0efcffa7da185bc0e2566657df8d3b2a811d7a60c981d37676de754169f463</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22930334$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pérez-Ruiz, Raúl</creatorcontrib><creatorcontrib>Sáez, Jose A</creatorcontrib><creatorcontrib>Domingo, Luis R</creatorcontrib><creatorcontrib>Jiménez, M Consuelo</creatorcontrib><creatorcontrib>Miranda, Miguel A</creatorcontrib><title>Ring splitting of azetidin-2-ones via radical anions</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.</description><subject>Anions - chemistry</subject><subject>Azetidines - chemical synthesis</subject><subject>Azetidines - chemistry</subject><subject>Free Radicals - chemistry</subject><subject>Molecular Structure</subject><subject>Quantum Theory</subject><subject>Ultraviolet Rays</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMtKw0AYRgdRbK1ufADJUoTRuWUuSyneoCCIrsOfuchIkqmZRNCnN6W1rr5vcTiLg9A5JdeUcHNjWaqZLJmGAzSnQilMSm4O95-RGTrJ-YMQapQUx2jGmOGEczFH4iV270VeN3EYNi-FAn78EF3sMMOp87n4ilD04KKFpoAupi6foqMATfZnu12gt_u71-UjXj0_PC1vV9gyrQbMZSA-2BBAOaC6rC3xrJRSlsoF7XjNQFPqFEhijaaOK6mk86oUVJogJF-gy6133afP0eehamO2vmmg82nMFSXSMKI4pxN6tUVtn3LufajWfWyh_56galOp-q80wRc771i33u3Rvyz8F34dYS8</recordid><startdate>20121021</startdate><enddate>20121021</enddate><creator>Pérez-Ruiz, Raúl</creator><creator>Sáez, Jose A</creator><creator>Domingo, Luis R</creator><creator>Jiménez, M Consuelo</creator><creator>Miranda, Miguel A</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20121021</creationdate><title>Ring splitting of azetidin-2-ones via radical anions</title><author>Pérez-Ruiz, Raúl ; Sáez, Jose A ; Domingo, Luis R ; Jiménez, M Consuelo ; Miranda, Miguel A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c287t-36f0efcffa7da185bc0e2566657df8d3b2a811d7a60c981d37676de754169f463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anions - chemistry</topic><topic>Azetidines - chemical synthesis</topic><topic>Azetidines - chemistry</topic><topic>Free Radicals - chemistry</topic><topic>Molecular Structure</topic><topic>Quantum Theory</topic><topic>Ultraviolet Rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pérez-Ruiz, Raúl</creatorcontrib><creatorcontrib>Sáez, Jose A</creatorcontrib><creatorcontrib>Domingo, Luis R</creatorcontrib><creatorcontrib>Jiménez, M Consuelo</creatorcontrib><creatorcontrib>Miranda, Miguel A</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pérez-Ruiz, Raúl</au><au>Sáez, Jose A</au><au>Domingo, Luis R</au><au>Jiménez, M Consuelo</au><au>Miranda, Miguel A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ring splitting of azetidin-2-ones via radical anions</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2012-10-21</date><risdate>2012</risdate><volume>10</volume><issue>39</issue><spage>7928</spage><epage>7932</epage><pages>7928-7932</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.</abstract><cop>England</cop><pmid>22930334</pmid><doi>10.1039/c2ob26528a</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2012-10, Vol.10 (39), p.7928-7932 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1069207331 |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Anions - chemistry Azetidines - chemical synthesis Azetidines - chemistry Free Radicals - chemistry Molecular Structure Quantum Theory Ultraviolet Rays |
| title | Ring splitting of azetidin-2-ones via radical anions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T00%3A31%3A58IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Ring%20splitting%20of%20azetidin-2-ones%20via%20radical%20anions&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=P%C3%A9rez-Ruiz,%20Ra%C3%BAl&rft.date=2012-10-21&rft.volume=10&rft.issue=39&rft.spage=7928&rft.epage=7932&rft.pages=7928-7932&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c2ob26528a&rft_dat=%3Cproquest_cross%3E1069207331%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1069207331&rft_id=info:pmid/22930334&rfr_iscdi=true |