Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione
Dibenzo[a,e]cyclooctene-5,6-dione ( 18 ), a derivative of 1,2-cyclooctatetraenoquinone ( 4 ), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one ( 26 ), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene ( 20 ) with dimet...
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| Veröffentlicht in: | Canadian journal of chemistry 1970-03, Vol.48 (5), p.788-795 |
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| container_title | Canadian journal of chemistry |
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| creator | Yates, Peter Lewars, Errol G McCabe, Peter H |
| description | Dibenzo[a,e]cyclooctene-5,6-dione (
18
), a derivative of 1,2-cyclooctatetraenoquinone (
4
), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one (
26
), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene (
20
) with dimethyl sulfoxide and collidine. Infrared and proton magnetic resonance spectroscopic studies have shown that the 8-membered ring of
18
is not aromatic. |
| doi_str_mv | 10.1139/v70-128 |
| format | Article |
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18
), a derivative of 1,2-cyclooctatetraenoquinone (
4
), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one (
26
), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene (
20
) with dimethyl sulfoxide and collidine. Infrared and proton magnetic resonance spectroscopic studies have shown that the 8-membered ring of
18
is not aromatic.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v70-128</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1970-03, Vol.48 (5), p.788-795</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c202f-43ef953f06c8f73c7ee7db061da7001125f921ddf807838f73328f593de459843</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v70-128$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v70-128$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,780,784,2932,27924,27925,64428,65234</link.rule.ids></links><search><creatorcontrib>Yates, Peter</creatorcontrib><creatorcontrib>Lewars, Errol G</creatorcontrib><creatorcontrib>McCabe, Peter H</creatorcontrib><title>Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Dibenzo[a,e]cyclooctene-5,6-dione (
18
), a derivative of 1,2-cyclooctatetraenoquinone (
4
), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one (
26
), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene (
20
) with dimethyl sulfoxide and collidine. Infrared and proton magnetic resonance spectroscopic studies have shown that the 8-membered ring of
18
is not aromatic.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1970</creationdate><recordtype>article</recordtype><recordid>eNp10EFLAzEQhuEgCtYq_oWcFKSpk2S3yR6lVC0UvNSTlCVNJnSlJjXZCvXXu6XFg-BpGHh4Dx8h1xyGnMvq_ksB40KfkB4vNDApKn5KegCgWQGFOCcXOb93rwJR9shivLPrGG1rWmyTwRA_t02IAfOQTul8hTTvQrvC3GRqgqO5TVvbbhPS6Klrlhi-45sZ4MIeOxiQlYMRc00XuSRn3qwzXh1vn7w-TubjZzZ7eZqOH2bMChCeFRJ9VUoPI6u9klYhKreEEXdGAXAuSl8J7pzXoLTcEym0LyvpsCgrXcg-uT10bYo5J_T1JjUfJu1qDvV-lbpbpe5W6eTNQYZkE2Y0ya5-8RHVG-c7ePc__Fv9AVMgcLg</recordid><startdate>19700301</startdate><enddate>19700301</enddate><creator>Yates, Peter</creator><creator>Lewars, Errol G</creator><creator>McCabe, Peter H</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19700301</creationdate><title>Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione</title><author>Yates, Peter ; Lewars, Errol G ; McCabe, Peter H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c202f-43ef953f06c8f73c7ee7db061da7001125f921ddf807838f73328f593de459843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1970</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yates, Peter</creatorcontrib><creatorcontrib>Lewars, Errol G</creatorcontrib><creatorcontrib>McCabe, Peter H</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yates, Peter</au><au>Lewars, Errol G</au><au>McCabe, Peter H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1970-03-01</date><risdate>1970</risdate><volume>48</volume><issue>5</issue><spage>788</spage><epage>795</epage><pages>788-795</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>Dibenzo[a,e]cyclooctene-5,6-dione (
18
), a derivative of 1,2-cyclooctatetraenoquinone (
4
), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one (
26
), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene (
20
) with dimethyl sulfoxide and collidine. Infrared and proton magnetic resonance spectroscopic studies have shown that the 8-membered ring of
18
is not aromatic.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v70-128</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Canadian journal of chemistry, 1970-03, Vol.48 (5), p.788-795 |
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| language | eng |
| recordid | cdi_crossref_primary_10_1139_v70_128 |
| source | NRC Research Press; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| title | Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione |
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