The reactivity of isocyanides with pentafluoropyridine
Reactivity of some isocyanides with pentafluoropyridine under basic conditions in dry dimethyl sulfoxide was investigated. The reaction of pentafluoropyridine with toluenesulfonylmethyl isocyanide (TosMIC) was less selective, but the reactions of other isocyanides with pentafluoropyridine gave the d...
Gespeichert in:
| Veröffentlicht in: | Monatshefte für Chemie 2021-11, Vol.152 (11), p.1369-1375 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1375 |
|---|---|
| container_issue | 11 |
| container_start_page | 1369 |
| container_title | Monatshefte für Chemie |
| container_volume | 152 |
| creator | Irani, Motahereh Ranjbar-Karimi, Reza Poorfreidoni, Alireza Mehrabi, Hossein |
| description | Reactivity of some isocyanides with pentafluoropyridine under basic conditions in dry dimethyl sulfoxide was investigated. The reaction of pentafluoropyridine with toluenesulfonylmethyl isocyanide (TosMIC) was less selective, but the reactions of other isocyanides with pentafluoropyridine gave the desired 2,3,5,6-tetrafluoro-
N
-substituted isonicotinamide. The structures of all the compounds were confirmed by IR,
1
H NMR,
19
F NMR, and
13
C NMR spectroscopy, X-ray crystallography as well as elemental analysis.
Graphic abstract |
| doi_str_mv | 10.1007/s00706-021-02856-x |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2585419192</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2585419192</sourcerecordid><originalsourceid>FETCH-LOGICAL-c319t-ce090c489e29955859df206451e986ce015f6b4cfef99d1efc1022f7f0fb89c23</originalsourceid><addsrcrecordid>eNp9kE9LxDAQxYMouK5-AU8Fz9FJmqTNURb_geBlPYduOnGzrE1Nurr99mat4M3DzDDMe2_gR8glg2sGUN2k3EBR4CxXLRXdH5EZE6WgQlTymMwAuKKai-qUnKW0gbwLKGdELddYRGzs4D_9MBbBFT4FOzadbzEVX35YFz12Q-O2uxBDP0bf-g7PyYlrtgkvfuecvN7fLReP9Pnl4Wlx-0xtyfRALYIGK2qNXGspa6lbx0EJyVDXKl-ZdGolrEOndcvQWQacu8qBW9Xa8nJOrqbcPoaPHabBbMIudvml4TlOMM30QcUnlY0hpYjO9NG_N3E0DMyBj5n4mMzH_PAx-2wqJ1PK4u4N41_0P65vFL1o9g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2585419192</pqid></control><display><type>article</type><title>The reactivity of isocyanides with pentafluoropyridine</title><source>Springer Nature - Complete Springer Journals</source><creator>Irani, Motahereh ; Ranjbar-Karimi, Reza ; Poorfreidoni, Alireza ; Mehrabi, Hossein</creator><creatorcontrib>Irani, Motahereh ; Ranjbar-Karimi, Reza ; Poorfreidoni, Alireza ; Mehrabi, Hossein</creatorcontrib><description>Reactivity of some isocyanides with pentafluoropyridine under basic conditions in dry dimethyl sulfoxide was investigated. The reaction of pentafluoropyridine with toluenesulfonylmethyl isocyanide (TosMIC) was less selective, but the reactions of other isocyanides with pentafluoropyridine gave the desired 2,3,5,6-tetrafluoro-
N
-substituted isonicotinamide. The structures of all the compounds were confirmed by IR,
1
H NMR,
19
F NMR, and
13
C NMR spectroscopy, X-ray crystallography as well as elemental analysis.
Graphic abstract</description><identifier>ISSN: 0026-9247</identifier><identifier>EISSN: 1434-4475</identifier><identifier>DOI: 10.1007/s00706-021-02856-x</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Analytical Chemistry ; Chemical analysis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Crystallography ; Dimethyl sulfoxide ; Inorganic Chemistry ; NMR spectroscopy ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Theoretical and Computational Chemistry</subject><ispartof>Monatshefte für Chemie, 2021-11, Vol.152 (11), p.1369-1375</ispartof><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2021</rights><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-ce090c489e29955859df206451e986ce015f6b4cfef99d1efc1022f7f0fb89c23</citedby><cites>FETCH-LOGICAL-c319t-ce090c489e29955859df206451e986ce015f6b4cfef99d1efc1022f7f0fb89c23</cites><orcidid>0000-0002-2599-7252</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00706-021-02856-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00706-021-02856-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27915,27916,41479,42548,51310</link.rule.ids></links><search><creatorcontrib>Irani, Motahereh</creatorcontrib><creatorcontrib>Ranjbar-Karimi, Reza</creatorcontrib><creatorcontrib>Poorfreidoni, Alireza</creatorcontrib><creatorcontrib>Mehrabi, Hossein</creatorcontrib><title>The reactivity of isocyanides with pentafluoropyridine</title><title>Monatshefte für Chemie</title><addtitle>Monatsh Chem</addtitle><description>Reactivity of some isocyanides with pentafluoropyridine under basic conditions in dry dimethyl sulfoxide was investigated. The reaction of pentafluoropyridine with toluenesulfonylmethyl isocyanide (TosMIC) was less selective, but the reactions of other isocyanides with pentafluoropyridine gave the desired 2,3,5,6-tetrafluoro-
N
-substituted isonicotinamide. The structures of all the compounds were confirmed by IR,
1
H NMR,
19
F NMR, and
13
C NMR spectroscopy, X-ray crystallography as well as elemental analysis.
Graphic abstract</description><subject>Analytical Chemistry</subject><subject>Chemical analysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Crystallography</subject><subject>Dimethyl sulfoxide</subject><subject>Inorganic Chemistry</subject><subject>NMR spectroscopy</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Theoretical and Computational Chemistry</subject><issn>0026-9247</issn><issn>1434-4475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kE9LxDAQxYMouK5-AU8Fz9FJmqTNURb_geBlPYduOnGzrE1Nurr99mat4M3DzDDMe2_gR8glg2sGUN2k3EBR4CxXLRXdH5EZE6WgQlTymMwAuKKai-qUnKW0gbwLKGdELddYRGzs4D_9MBbBFT4FOzadbzEVX35YFz12Q-O2uxBDP0bf-g7PyYlrtgkvfuecvN7fLReP9Pnl4Wlx-0xtyfRALYIGK2qNXGspa6lbx0EJyVDXKl-ZdGolrEOndcvQWQacu8qBW9Xa8nJOrqbcPoaPHabBbMIudvml4TlOMM30QcUnlY0hpYjO9NG_N3E0DMyBj5n4mMzH_PAx-2wqJ1PK4u4N41_0P65vFL1o9g</recordid><startdate>20211101</startdate><enddate>20211101</enddate><creator>Irani, Motahereh</creator><creator>Ranjbar-Karimi, Reza</creator><creator>Poorfreidoni, Alireza</creator><creator>Mehrabi, Hossein</creator><general>Springer Vienna</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2599-7252</orcidid></search><sort><creationdate>20211101</creationdate><title>The reactivity of isocyanides with pentafluoropyridine</title><author>Irani, Motahereh ; Ranjbar-Karimi, Reza ; Poorfreidoni, Alireza ; Mehrabi, Hossein</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-ce090c489e29955859df206451e986ce015f6b4cfef99d1efc1022f7f0fb89c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Analytical Chemistry</topic><topic>Chemical analysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Crystallography</topic><topic>Dimethyl sulfoxide</topic><topic>Inorganic Chemistry</topic><topic>NMR spectroscopy</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Irani, Motahereh</creatorcontrib><creatorcontrib>Ranjbar-Karimi, Reza</creatorcontrib><creatorcontrib>Poorfreidoni, Alireza</creatorcontrib><creatorcontrib>Mehrabi, Hossein</creatorcontrib><collection>CrossRef</collection><jtitle>Monatshefte für Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Irani, Motahereh</au><au>Ranjbar-Karimi, Reza</au><au>Poorfreidoni, Alireza</au><au>Mehrabi, Hossein</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The reactivity of isocyanides with pentafluoropyridine</atitle><jtitle>Monatshefte für Chemie</jtitle><stitle>Monatsh Chem</stitle><date>2021-11-01</date><risdate>2021</risdate><volume>152</volume><issue>11</issue><spage>1369</spage><epage>1375</epage><pages>1369-1375</pages><issn>0026-9247</issn><eissn>1434-4475</eissn><abstract>Reactivity of some isocyanides with pentafluoropyridine under basic conditions in dry dimethyl sulfoxide was investigated. The reaction of pentafluoropyridine with toluenesulfonylmethyl isocyanide (TosMIC) was less selective, but the reactions of other isocyanides with pentafluoropyridine gave the desired 2,3,5,6-tetrafluoro-
N
-substituted isonicotinamide. The structures of all the compounds were confirmed by IR,
1
H NMR,
19
F NMR, and
13
C NMR spectroscopy, X-ray crystallography as well as elemental analysis.
Graphic abstract</abstract><cop>Vienna</cop><pub>Springer Vienna</pub><doi>10.1007/s00706-021-02856-x</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-2599-7252</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0026-9247 |
| ispartof | Monatshefte für Chemie, 2021-11, Vol.152 (11), p.1369-1375 |
| issn | 0026-9247 1434-4475 |
| language | eng |
| recordid | cdi_proquest_journals_2585419192 |
| source | Springer Nature - Complete Springer Journals |
| subjects | Analytical Chemistry Chemical analysis Chemistry Chemistry and Materials Science Chemistry/Food Science Crystallography Dimethyl sulfoxide Inorganic Chemistry NMR spectroscopy Organic Chemistry Original Paper Physical Chemistry Theoretical and Computational Chemistry |
| title | The reactivity of isocyanides with pentafluoropyridine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T05%3A01%3A42IST&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=The%20reactivity%20of%20isocyanides%20with%20pentafluoropyridine&rft.jtitle=Monatshefte%20f%C3%BCr%20Chemie&rft.au=Irani,%20Motahereh&rft.date=2021-11-01&rft.volume=152&rft.issue=11&rft.spage=1369&rft.epage=1375&rft.pages=1369-1375&rft.issn=0026-9247&rft.eissn=1434-4475&rft_id=info:doi/10.1007/s00706-021-02856-x&rft_dat=%3Cproquest_cross%3E2585419192%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=2585419192&rft_id=info:pmid/&rfr_iscdi=true |