The DielsAlder reactions of quinone imine ketals
N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth DielsAlder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pr...
Gespeichert in:
| Veröffentlicht in: | Canadian journal of chemistry 2004-02, Vol.82 (2), p.131-138 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 138 |
|---|---|
| container_issue | 2 |
| container_start_page | 131 |
| container_title | Canadian journal of chemistry |
| container_volume | 82 |
| creator | Banfield, Scott C Kerr, Michael A |
| description | N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth DielsAlder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pressures for cycloadditions while the N-tosyl and N-nosyl derivatives proceed under thermal (ambient pressure) conditions. In all cases the cycloadditions are completely regioselective.Key words: DielsAlder, quinone imine ketal, hyperbaric chemistry. |
| doi_str_mv | 10.1139/v03-188 |
| format | Article |
| fullrecord | <record><control><sourceid>crossref_nrcre</sourceid><recordid>TN_cdi_nrcresearch_primary_10_1139_v03_188</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1139_v03_188</sourcerecordid><originalsourceid>FETCH-LOGICAL-c380t-84d623a83e73a304d574f055a17f59dcf26f41a5514124a148bcb5a29f6d02d03</originalsourceid><addsrcrecordid>eNp1j8tKAzEUhoMoOFbxFbJSEKInt5nMstQrFNzUdUhzodHpTE1GwRfxgXwyIy0uBDfn58DHz_8hdErhklLeXr0DJ1SpPVRRoYBw1tJ9VAGAIgIEO0RHOT-XtwEmK8QWK4-vo-_y1-e0cz7h5I0d49BnPAT8-hb7ofc4rmO5L340XT5GB6GEP9nlBD3d3ixm92T-ePcwm86J5QpGooSrGTeK-4YbDsLJRgSQ0tAmyNbZwOogqJGSCsqEKWOXdikNa0PtgDngE3S-7bVpyDn5oDcprk360BT0j6ouqrqoFvJsS_bJJp-9SXb1C-8gvXGhgBf_g39bvwGKpmDv</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>The DielsAlder reactions of quinone imine ketals</title><source>Free Full-Text Journals in Chemistry</source><creator>Banfield, Scott C ; Kerr, Michael A</creator><creatorcontrib>Banfield, Scott C ; Kerr, Michael A</creatorcontrib><description>N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth DielsAlder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pressures for cycloadditions while the N-tosyl and N-nosyl derivatives proceed under thermal (ambient pressure) conditions. In all cases the cycloadditions are completely regioselective.Key words: DielsAlder, quinone imine ketal, hyperbaric chemistry.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v03-188</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 2004-02, Vol.82 (2), p.131-138</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c380t-84d623a83e73a304d574f055a17f59dcf26f41a5514124a148bcb5a29f6d02d03</citedby><cites>FETCH-LOGICAL-c380t-84d623a83e73a304d574f055a17f59dcf26f41a5514124a148bcb5a29f6d02d03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Banfield, Scott C</creatorcontrib><creatorcontrib>Kerr, Michael A</creatorcontrib><title>The DielsAlder reactions of quinone imine ketals</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth DielsAlder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pressures for cycloadditions while the N-tosyl and N-nosyl derivatives proceed under thermal (ambient pressure) conditions. In all cases the cycloadditions are completely regioselective.Key words: DielsAlder, quinone imine ketal, hyperbaric chemistry.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNp1j8tKAzEUhoMoOFbxFbJSEKInt5nMstQrFNzUdUhzodHpTE1GwRfxgXwyIy0uBDfn58DHz_8hdErhklLeXr0DJ1SpPVRRoYBw1tJ9VAGAIgIEO0RHOT-XtwEmK8QWK4-vo-_y1-e0cz7h5I0d49BnPAT8-hb7ofc4rmO5L340XT5GB6GEP9nlBD3d3ixm92T-ePcwm86J5QpGooSrGTeK-4YbDsLJRgSQ0tAmyNbZwOogqJGSCsqEKWOXdikNa0PtgDngE3S-7bVpyDn5oDcprk360BT0j6ouqrqoFvJsS_bJJp-9SXb1C-8gvXGhgBf_g39bvwGKpmDv</recordid><startdate>20040201</startdate><enddate>20040201</enddate><creator>Banfield, Scott C</creator><creator>Kerr, Michael A</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20040201</creationdate><title>The DielsAlder reactions of quinone imine ketals</title><author>Banfield, Scott C ; Kerr, Michael A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-84d623a83e73a304d574f055a17f59dcf26f41a5514124a148bcb5a29f6d02d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Banfield, Scott C</creatorcontrib><creatorcontrib>Kerr, Michael A</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Banfield, Scott C</au><au>Kerr, Michael A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The DielsAlder reactions of quinone imine ketals</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>2004-02-01</date><risdate>2004</risdate><volume>82</volume><issue>2</issue><spage>131</spage><epage>138</epage><pages>131-138</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth DielsAlder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalenes. The N-benzoyl derivatives require high pressures for cycloadditions while the N-tosyl and N-nosyl derivatives proceed under thermal (ambient pressure) conditions. In all cases the cycloadditions are completely regioselective.Key words: DielsAlder, quinone imine ketal, hyperbaric chemistry.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v03-188</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 2004-02, Vol.82 (2), p.131-138 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_nrcresearch_primary_10_1139_v03_188 |
| source | Free Full-Text Journals in Chemistry |
| title | The DielsAlder reactions of quinone imine ketals |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T19%3A39%3A58IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref_nrcre&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20Diels%C2%96Alder%20reactions%20of%20quinone%20imine%20ketals&rft.jtitle=Canadian%20journal%20of%20chemistry&rft.au=Banfield,%20Scott%20C&rft.date=2004-02-01&rft.volume=82&rft.issue=2&rft.spage=131&rft.epage=138&rft.pages=131-138&rft.issn=0008-4042&rft.eissn=1480-3291&rft_id=info:doi/10.1139/v03-188&rft_dat=%3Ccrossref_nrcre%3E10_1139_v03_188%3C/crossref_nrcre%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |