Trifluoromethyl derivatives of pentacyclo[5.4.0.02,6.03,10.05,9]undecane
Three cage‐like polycyclic compounds, viz.exo‐8‐(trifluoromethyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐endo‐8‐ol, C12H13F3O, 5‐(trifluoromethyl)‐4‐oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecan‐3‐ol, C12H11F3O2, and N‐[exo‐11‐(trifluoromethyl)‐endo‐11‐(trimethylsilyloxy)pentacy...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2005-04, Vol.61 (4), p.o221-o226 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
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| creator | Linden, Anthony Romański, Jarosław Mlostoń, Grzegorz Heimgartner, Heinz |
| description | Three cage‐like polycyclic compounds, viz.exo‐8‐(trifluoromethyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐endo‐8‐ol, C12H13F3O, 5‐(trifluoromethyl)‐4‐oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecan‐3‐ol, C12H11F3O2, and N‐[exo‐11‐(trifluoromethyl)‐endo‐11‐(trimethylsilyloxy)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐8‐ylidene]aniline methanol solvate, C21H24F3NOSi·CH4O, were obtained from the corresponding oxo derivatives by nucleophilic trifluoromethylation with (trifluoromethyl)trimethylsilane in 1,2‐dimethoxyethane solution in the presence of CsF. The crystal structures show that the addition of trifluoromethanide occurs exclusively from the exo face of the polycyclic ketones. Further examination of the crystal structures, together with that of the starting pentacyclo[5.4.0.02,6.03,10.05,9]undecane‐8,11‐dione, C11H10O2, showed that increasing substitution at the 8‐ and/or 11‐positions in the cage molecules increases the non‐bonded intramolecular C·C distances at the mouth of the cage and changes the puckering of the five‐membered rings involving the 8‐ and 11‐positions from an envelope towards a distorted half‐chair conformation. Intermolecular co‐operative O—H·O hydrogen bonds in the endo‐8‐ol compound link the molecules into tetramers. |
| doi_str_mv | 10.1107/S0108270105004701 |
| format | Article |
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The crystal structures show that the addition of trifluoromethanide occurs exclusively from the exo face of the polycyclic ketones. Further examination of the crystal structures, together with that of the starting pentacyclo[5.4.0.02,6.03,10.05,9]undecane‐8,11‐dione, C11H10O2, showed that increasing substitution at the 8‐ and/or 11‐positions in the cage molecules increases the non‐bonded intramolecular C·C distances at the mouth of the cage and changes the puckering of the five‐membered rings involving the 8‐ and 11‐positions from an envelope towards a distorted half‐chair conformation. Intermolecular co‐operative O—H·O hydrogen bonds in the endo‐8‐ol compound link the molecules into tetramers.</description><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S0108270105004701</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: Munksgaard International Publishers</publisher><subject>Chemical compounds ; Crystal structure ; Hydrogen bonds</subject><ispartof>Acta crystallographica. 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Section C, Crystal structure communications</title><addtitle>Acta Cryst. C</addtitle><description>Three cage‐like polycyclic compounds, viz.exo‐8‐(trifluoromethyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐endo‐8‐ol, C12H13F3O, 5‐(trifluoromethyl)‐4‐oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecan‐3‐ol, C12H11F3O2, and N‐[exo‐11‐(trifluoromethyl)‐endo‐11‐(trimethylsilyloxy)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐8‐ylidene]aniline methanol solvate, C21H24F3NOSi·CH4O, were obtained from the corresponding oxo derivatives by nucleophilic trifluoromethylation with (trifluoromethyl)trimethylsilane in 1,2‐dimethoxyethane solution in the presence of CsF. The crystal structures show that the addition of trifluoromethanide occurs exclusively from the exo face of the polycyclic ketones. Further examination of the crystal structures, together with that of the starting pentacyclo[5.4.0.02,6.03,10.05,9]undecane‐8,11‐dione, C11H10O2, showed that increasing substitution at the 8‐ and/or 11‐positions in the cage molecules increases the non‐bonded intramolecular C·C distances at the mouth of the cage and changes the puckering of the five‐membered rings involving the 8‐ and 11‐positions from an envelope towards a distorted half‐chair conformation. Intermolecular co‐operative O—H·O hydrogen bonds in the endo‐8‐ol compound link the molecules into tetramers.</description><subject>Chemical compounds</subject><subject>Crystal structure</subject><subject>Hydrogen bonds</subject><issn>0108-2701</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNplkMFOwkAQhjdGExF9AG_EM62z2-5290iIooKaCIYYYzZLO43FQnHbon0oXoIncwnGi5f5D__3z0x-Qs4p-JRCdDkGCpJFbnKA0OkBaVEB4PGIq0PS2tnezj8mJ2U5BwDGWNAiTxObpXld2GK7WWD1vt00eSdBm61Nla2x7BRpZ4XLymw3cRPnjnrlfuiDD6wrfAi67gHgXfVWLxOMHbXEU3KUmrzEs19tk-frq0n_xhs9Dm77vZGXURoKj6MSaJDHAoRJYpOmwsiZYpwpkAkCp2wmIeVKoREyiYwxYQyQmhmN0SgatMnFfu_KFp81lpWeF7VdupOaQUBDxpV0kNxDX1mOjV7ZbGFsoynoXW36X22699IfD6mkwkW9fTQrK_z-ixr7oUUURFxPHwb6bjDiw_H9VLPgB6bmcow</recordid><startdate>200504</startdate><enddate>200504</enddate><creator>Linden, Anthony</creator><creator>Romański, Jarosław</creator><creator>Mlostoń, Grzegorz</creator><creator>Heimgartner, Heinz</creator><general>Munksgaard International Publishers</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>200504</creationdate><title>Trifluoromethyl derivatives of pentacyclo[5.4.0.02,6.03,10.05,9]undecane</title><author>Linden, Anthony ; Romański, Jarosław ; Mlostoń, Grzegorz ; Heimgartner, Heinz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i1146-5e96eae5c606adcaff6a8b9252908de0512b80f599ea68d7aaa4c00fab1cea913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemical compounds</topic><topic>Crystal structure</topic><topic>Hydrogen bonds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Linden, Anthony</creatorcontrib><creatorcontrib>Romański, Jarosław</creatorcontrib><creatorcontrib>Mlostoń, Grzegorz</creatorcontrib><creatorcontrib>Heimgartner, Heinz</creatorcontrib><collection>Istex</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Linden, Anthony</au><au>Romański, Jarosław</au><au>Mlostoń, Grzegorz</au><au>Heimgartner, Heinz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Trifluoromethyl derivatives of pentacyclo[5.4.0.02,6.03,10.05,9]undecane</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Cryst. C</addtitle><date>2005-04</date><risdate>2005</risdate><volume>61</volume><issue>4</issue><spage>o221</spage><epage>o226</epage><pages>o221-o226</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><abstract>Three cage‐like polycyclic compounds, viz.exo‐8‐(trifluoromethyl)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐endo‐8‐ol, C12H13F3O, 5‐(trifluoromethyl)‐4‐oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecan‐3‐ol, C12H11F3O2, and N‐[exo‐11‐(trifluoromethyl)‐endo‐11‐(trimethylsilyloxy)pentacyclo[5.4.0.02,6.03,10.05,9]undecan‐8‐ylidene]aniline methanol solvate, C21H24F3NOSi·CH4O, were obtained from the corresponding oxo derivatives by nucleophilic trifluoromethylation with (trifluoromethyl)trimethylsilane in 1,2‐dimethoxyethane solution in the presence of CsF. The crystal structures show that the addition of trifluoromethanide occurs exclusively from the exo face of the polycyclic ketones. Further examination of the crystal structures, together with that of the starting pentacyclo[5.4.0.02,6.03,10.05,9]undecane‐8,11‐dione, C11H10O2, showed that increasing substitution at the 8‐ and/or 11‐positions in the cage molecules increases the non‐bonded intramolecular C·C distances at the mouth of the cage and changes the puckering of the five‐membered rings involving the 8‐ and 11‐positions from an envelope towards a distorted half‐chair conformation. Intermolecular co‐operative O—H·O hydrogen bonds in the endo‐8‐ol compound link the molecules into tetramers.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>Munksgaard International Publishers</pub><doi>10.1107/S0108270105004701</doi></addata></record> |
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| subjects | Chemical compounds Crystal structure Hydrogen bonds |
| title | Trifluoromethyl derivatives of pentacyclo[5.4.0.02,6.03,10.05,9]undecane |
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