A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr
The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H 2 O and H 2 O—Bu t OH have been studied for the first time. It was found that NiO(OH) is efficient with respect to anilines with one donor (Me, OMe) or one weak acceptor (Cl, Br) substituent in the benzen...
Gespeichert in:
| Veröffentlicht in: | Russian chemical bulletin 2023-09, Vol.72 (9), p.2095-2101 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2101 |
|---|---|
| container_issue | 9 |
| container_start_page | 2095 |
| container_title | Russian chemical bulletin |
| container_volume | 72 |
| creator | Sigacheva, V. L. Kokorekin, V. A. Gorpinchenko, N. V. Lyalin, B. V. |
| description | The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H
2
O and H
2
O—Bu
t
OH have been studied for the first time. It was found that NiO(OH) is efficient with respect to anilines with one donor (Me, OMe) or one weak acceptor (Cl, Br) substituent in the benzene ring, while NaOCl and NaOBr are more active towards anilines with one strong acceptor (CN, NO
2
) or several weak acceptor (Cl) substituents. Based on the results obtained, an approach has been proposed to the two-stage synthesis of a number of azobenzenes under mild conditions with a yield of up to 48%. |
| doi_str_mv | 10.1007/s11172-023-4004-x |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2869266377</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2869266377</sourcerecordid><originalsourceid>FETCH-LOGICAL-c268t-89621f01fb0beb17ae0660359adc87544d2d1443c8b034e68eff31ea2bbfa4493</originalsourceid><addsrcrecordid>eNp1kbFOwzAURSMEEqXwAWyWWEBqwHacxBlLBRSpShaYLSd5aVMFO9gptJ34CHb-jS_BbZCYmN6V3j33yb6ed07wNcE4vrGEkJj6mAY-w5j56wNvQMI48BMSk0OncRT5IeXhsXdi7RJjTDnnA-9rjBS8I9m2RstigTqNugUgu1Fu2NoiXSG51TmoLSiwKJcWSqTV3qXXdSm7-g1Q-v3xmaJCr9qmVvM9pGonHbFSJZi9XRZd7Ui3hAaKzui5izSyc4FpnV1m06sRSmU2aUaOLnfy1px6R5VsLJz9zqH3fH_3NJn6s-zhcTKe-QWNeOfzJKKkwqTKcQ45iSW49-IgTGRZ8DhkrKQlYSwoeI4DBhGHqgoISJrnlWQsCYbeRZ_r_uF1BbYTS70yyp0UlEcJjaIgjp2L9K7CaGsNVKI19Ys0G0Gw2PUg-h6E60HsehBrx9Cesc6r5mD-kv-HfgD0PI0R</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2869266377</pqid></control><display><type>article</type><title>A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr</title><source>SpringerLink Journals - AutoHoldings</source><creator>Sigacheva, V. L. ; Kokorekin, V. A. ; Gorpinchenko, N. V. ; Lyalin, B. V.</creator><creatorcontrib>Sigacheva, V. L. ; Kokorekin, V. A. ; Gorpinchenko, N. V. ; Lyalin, B. V.</creatorcontrib><description>The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H
2
O and H
2
O—Bu
t
OH have been studied for the first time. It was found that NiO(OH) is efficient with respect to anilines with one donor (Me, OMe) or one weak acceptor (Cl, Br) substituent in the benzene ring, while NaOCl and NaOBr are more active towards anilines with one strong acceptor (CN, NO
2
) or several weak acceptor (Cl) substituents. Based on the results obtained, an approach has been proposed to the two-stage synthesis of a number of azobenzenes under mild conditions with a yield of up to 48%.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-023-4004-x</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Aniline ; Benzene ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Full Articles ; Inorganic Chemistry ; Nickel oxides ; Nitrogen dioxide ; Organic Chemistry ; Sodium hypochlorite ; Synthesis</subject><ispartof>Russian chemical bulletin, 2023-09, Vol.72 (9), p.2095-2101</ispartof><rights>Springer Science+Business Media LLC 2023</rights><rights>Springer Science+Business Media LLC 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c268t-89621f01fb0beb17ae0660359adc87544d2d1443c8b034e68eff31ea2bbfa4493</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-023-4004-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-023-4004-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Sigacheva, V. L.</creatorcontrib><creatorcontrib>Kokorekin, V. A.</creatorcontrib><creatorcontrib>Gorpinchenko, N. V.</creatorcontrib><creatorcontrib>Lyalin, B. V.</creatorcontrib><title>A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H
2
O and H
2
O—Bu
t
OH have been studied for the first time. It was found that NiO(OH) is efficient with respect to anilines with one donor (Me, OMe) or one weak acceptor (Cl, Br) substituent in the benzene ring, while NaOCl and NaOBr are more active towards anilines with one strong acceptor (CN, NO
2
) or several weak acceptor (Cl) substituents. Based on the results obtained, an approach has been proposed to the two-stage synthesis of a number of azobenzenes under mild conditions with a yield of up to 48%.</description><subject>Aniline</subject><subject>Benzene</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Nickel oxides</subject><subject>Nitrogen dioxide</subject><subject>Organic Chemistry</subject><subject>Sodium hypochlorite</subject><subject>Synthesis</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kbFOwzAURSMEEqXwAWyWWEBqwHacxBlLBRSpShaYLSd5aVMFO9gptJ34CHb-jS_BbZCYmN6V3j33yb6ed07wNcE4vrGEkJj6mAY-w5j56wNvQMI48BMSk0OncRT5IeXhsXdi7RJjTDnnA-9rjBS8I9m2RstigTqNugUgu1Fu2NoiXSG51TmoLSiwKJcWSqTV3qXXdSm7-g1Q-v3xmaJCr9qmVvM9pGonHbFSJZi9XRZd7Ui3hAaKzui5izSyc4FpnV1m06sRSmU2aUaOLnfy1px6R5VsLJz9zqH3fH_3NJn6s-zhcTKe-QWNeOfzJKKkwqTKcQ45iSW49-IgTGRZ8DhkrKQlYSwoeI4DBhGHqgoISJrnlWQsCYbeRZ_r_uF1BbYTS70yyp0UlEcJjaIgjp2L9K7CaGsNVKI19Ys0G0Gw2PUg-h6E60HsehBrx9Cesc6r5mD-kv-HfgD0PI0R</recordid><startdate>20230901</startdate><enddate>20230901</enddate><creator>Sigacheva, V. L.</creator><creator>Kokorekin, V. A.</creator><creator>Gorpinchenko, N. V.</creator><creator>Lyalin, B. V.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20230901</creationdate><title>A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr</title><author>Sigacheva, V. L. ; Kokorekin, V. A. ; Gorpinchenko, N. V. ; Lyalin, B. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c268t-89621f01fb0beb17ae0660359adc87544d2d1443c8b034e68eff31ea2bbfa4493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aniline</topic><topic>Benzene</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Nickel oxides</topic><topic>Nitrogen dioxide</topic><topic>Organic Chemistry</topic><topic>Sodium hypochlorite</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sigacheva, V. L.</creatorcontrib><creatorcontrib>Kokorekin, V. A.</creatorcontrib><creatorcontrib>Gorpinchenko, N. V.</creatorcontrib><creatorcontrib>Lyalin, B. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sigacheva, V. L.</au><au>Kokorekin, V. A.</au><au>Gorpinchenko, N. V.</au><au>Lyalin, B. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2023-09-01</date><risdate>2023</risdate><volume>72</volume><issue>9</issue><spage>2095</spage><epage>2101</epage><pages>2095-2101</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>The patterns of the reactions of anilines with NiO(OH), NaOCl, and NaOBr electro-generated in H
2
O and H
2
O—Bu
t
OH have been studied for the first time. It was found that NiO(OH) is efficient with respect to anilines with one donor (Me, OMe) or one weak acceptor (Cl, Br) substituent in the benzene ring, while NaOCl and NaOBr are more active towards anilines with one strong acceptor (CN, NO
2
) or several weak acceptor (Cl) substituents. Based on the results obtained, an approach has been proposed to the two-stage synthesis of a number of azobenzenes under mild conditions with a yield of up to 48%.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-023-4004-x</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1066-5285 |
| ispartof | Russian chemical bulletin, 2023-09, Vol.72 (9), p.2095-2101 |
| issn | 1066-5285 1573-9171 |
| language | eng |
| recordid | cdi_proquest_journals_2869266377 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Aniline Benzene Chemistry Chemistry and Materials Science Chemistry/Food Science Full Articles Inorganic Chemistry Nickel oxides Nitrogen dioxide Organic Chemistry Sodium hypochlorite Synthesis |
| title | A new approach to the synthesis of azobenzenes based on the oxidative N—N coupling of anilines under the action of electrogenerated NiO(OH), NaOCl, and NaOBr |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T11%3A44%3A29IST&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=A%20new%20approach%20to%20the%20synthesis%20of%20azobenzenes%20based%20on%20the%20oxidative%20N%E2%80%94N%20coupling%20of%20anilines%20under%20the%20action%20of%20electrogenerated%20NiO(OH),%20NaOCl,%20and%20NaOBr&rft.jtitle=Russian%20chemical%20bulletin&rft.au=Sigacheva,%20V.%20L.&rft.date=2023-09-01&rft.volume=72&rft.issue=9&rft.spage=2095&rft.epage=2101&rft.pages=2095-2101&rft.issn=1066-5285&rft.eissn=1573-9171&rft_id=info:doi/10.1007/s11172-023-4004-x&rft_dat=%3Cproquest_cross%3E2869266377%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=2869266377&rft_id=info:pmid/&rfr_iscdi=true |