Synthesis of 2,3,6,7,8,9-Hexahydro-1 H -cyclohepta[ gh ]phenalene
2,3,6,7,8,9-Hexahydro-1H-cyclohepta[gh]phenalene (7) has been prepared via the tricyclic ketone 3-oxo-1,2,3,7,8,9,10,10a-octahydrocyclohepta[de]naphthalene (1) and the tetracyclic ketone 1-oxo-2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (6). Conversion of the tricyclic ketone 1 into 1-oxo-1,2,3...
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| Veröffentlicht in: | Canadian journal of chemistry 1971-05, Vol.49 (9), p.1343-1349 |
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| container_title | Canadian journal of chemistry |
| container_volume | 49 |
| creator | Fischer, A. Leonard, D. R. A. Happer, D. A. R. |
| description | 2,3,6,7,8,9-Hexahydro-1H-cyclohepta[gh]phenalene (7) has been prepared via the tricyclic ketone 3-oxo-1,2,3,7,8,9,10,10a-octahydrocyclohepta[de]naphthalene (1) and the tetracyclic ketone 1-oxo-2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (6). Conversion of the tricyclic ketone 1 into 1-oxo-1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (8) and reduction of this tetracyclic ketone to 1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (9), followed by aromatization, gave 5,5a,6,7,8,9-hexahydro-4H-cyclohepta[cd]phenalene (10) (73 %) together with the desired isomeric 2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (7) (23%). |
| doi_str_mv | 10.1139/v71-223 |
| format | Article |
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R. A. ; Happer, D. A. R.</creator><creatorcontrib>Fischer, A. ; Leonard, D. R. A. ; Happer, D. A. R.</creatorcontrib><description>2,3,6,7,8,9-Hexahydro-1H-cyclohepta[gh]phenalene (7) has been prepared via the tricyclic ketone 3-oxo-1,2,3,7,8,9,10,10a-octahydrocyclohepta[de]naphthalene (1) and the tetracyclic ketone 1-oxo-2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (6). Conversion of the tricyclic ketone 1 into 1-oxo-1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (8) and reduction of this tetracyclic ketone to 1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (9), followed by aromatization, gave 5,5a,6,7,8,9-hexahydro-4H-cyclohepta[cd]phenalene (10) (73 %) together with the desired isomeric 2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (7) (23%).</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v71-223</identifier><language>eng</language><ispartof>Canadian journal of chemistry, 1971-05, Vol.49 (9), p.1343-1349</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c703-b72193b39fdb7edec13e7590063c67aec0330091380038b36570730ff54ecf43</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids></links><search><creatorcontrib>Fischer, A.</creatorcontrib><creatorcontrib>Leonard, D. R. A.</creatorcontrib><creatorcontrib>Happer, D. A. R.</creatorcontrib><title>Synthesis of 2,3,6,7,8,9-Hexahydro-1 H -cyclohepta[ gh ]phenalene</title><title>Canadian journal of chemistry</title><description>2,3,6,7,8,9-Hexahydro-1H-cyclohepta[gh]phenalene (7) has been prepared via the tricyclic ketone 3-oxo-1,2,3,7,8,9,10,10a-octahydrocyclohepta[de]naphthalene (1) and the tetracyclic ketone 1-oxo-2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (6). Conversion of the tricyclic ketone 1 into 1-oxo-1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (8) and reduction of this tetracyclic ketone to 1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (9), followed by aromatization, gave 5,5a,6,7,8,9-hexahydro-4H-cyclohepta[cd]phenalene (10) (73 %) together with the desired isomeric 2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (7) (23%).</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1971</creationdate><recordtype>article</recordtype><recordid>eNotz8FKxDAUheEgCtZRfIXs3DR6b27bNMthUCsMuBh3IiVNb-zI2JZmEPv2VnR1-DcHPiGuEW4Ryd59GVRa04lIMCtBkbZ4KhIAKFUGmT4XFzF-LGlA54lY7-b-2HHcRzkEqVNKi9SkZWpVxd-um9tpUCgrqfzsD0PH49G9yvdOvo0d9-7APV-Ks-AOka_-dyV2D_cvm0ptnx-fNuut8gZINUajpYZsaBvDLXskNrkFKMgXxrEHIgCLVAJQ2VCRGzAEIeQZ-5DRStz8vfppiHHiUI_T_tNNc41Q_7rrxV0vbvoBo59Glg</recordid><startdate>19710501</startdate><enddate>19710501</enddate><creator>Fischer, A.</creator><creator>Leonard, D. R. A.</creator><creator>Happer, D. A. R.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19710501</creationdate><title>Synthesis of 2,3,6,7,8,9-Hexahydro-1 H -cyclohepta[ gh ]phenalene</title><author>Fischer, A. ; Leonard, D. R. A. ; Happer, D. A. R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c703-b72193b39fdb7edec13e7590063c67aec0330091380038b36570730ff54ecf43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1971</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fischer, A.</creatorcontrib><creatorcontrib>Leonard, D. R. A.</creatorcontrib><creatorcontrib>Happer, D. A. R.</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fischer, A.</au><au>Leonard, D. R. A.</au><au>Happer, D. A. R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2,3,6,7,8,9-Hexahydro-1 H -cyclohepta[ gh ]phenalene</atitle><jtitle>Canadian journal of chemistry</jtitle><date>1971-05-01</date><risdate>1971</risdate><volume>49</volume><issue>9</issue><spage>1343</spage><epage>1349</epage><pages>1343-1349</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>2,3,6,7,8,9-Hexahydro-1H-cyclohepta[gh]phenalene (7) has been prepared via the tricyclic ketone 3-oxo-1,2,3,7,8,9,10,10a-octahydrocyclohepta[de]naphthalene (1) and the tetracyclic ketone 1-oxo-2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (6). Conversion of the tricyclic ketone 1 into 1-oxo-1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (8) and reduction of this tetracyclic ketone to 1,2,3,3a,5,5a,6,7,8,9-decahydro-4H-cyclohepta[cd]phenalene (9), followed by aromatization, gave 5,5a,6,7,8,9-hexahydro-4H-cyclohepta[cd]phenalene (10) (73 %) together with the desired isomeric 2,3,6,7,8,9-hexahydro-1H-cyclohepta[gh]phenalene (7) (23%).</abstract><doi>10.1139/v71-223</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| title | Synthesis of 2,3,6,7,8,9-Hexahydro-1 H -cyclohepta[ gh ]phenalene |
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