Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study
A series of calix[4]arenes bearing various substituents including alkyl, p-bromobenzyl, carboxy and allyl at opposite methylene bridges has been synthesized via successive metallation followed by nucleophilic substitution. In a first step, mono-lithiated calix[4]arenes react with terminal bromoalkan...
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| Veröffentlicht in: | Tetrahedron 2011-08, Vol.67 (31), p.5656-5662 |
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| container_title | Tetrahedron |
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| creator | Fischer, Conrad Lin, Guisheng Seichter, Wilhelm Weber, Edwin |
| description | A series of calix[4]arenes bearing various substituents including alkyl,
p-bromobenzyl, carboxy and allyl at opposite methylene bridges has been synthesized via successive metallation followed by nucleophilic substitution. In a first step, mono-lithiated calix[4]arenes react with terminal bromoalkanes to give 2-alkylated calix[4]arenes or with CO
2 the respective calixarene-2-carboxylic acid in good yields. A second lithiation step of the monosubstituted products with subsequent attachment of both polar and non-polar substituents yields several new diametrally bridge-disubstituted calix[4]arenes. 2D-NMR measurements establish the disubstituted calixarenes to predominantly adopt the 1,2-
alternate conformation in solution. First examples of X-ray crystal structures of the new type of disubstituted calix[4]arenes are described featuring the calix[4]arene also in the rare 1,2-
alternate conformation.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.05.087 |
| format | Article |
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p-bromobenzyl, carboxy and allyl at opposite methylene bridges has been synthesized via successive metallation followed by nucleophilic substitution. In a first step, mono-lithiated calix[4]arenes react with terminal bromoalkanes to give 2-alkylated calix[4]arenes or with CO
2 the respective calixarene-2-carboxylic acid in good yields. A second lithiation step of the monosubstituted products with subsequent attachment of both polar and non-polar substituents yields several new diametrally bridge-disubstituted calix[4]arenes. 2D-NMR measurements establish the disubstituted calixarenes to predominantly adopt the 1,2-
alternate conformation in solution. First examples of X-ray crystal structures of the new type of disubstituted calix[4]arenes are described featuring the calix[4]arene also in the rare 1,2-
alternate conformation.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.05.087</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Allyl compounds ; Attachment ; Bridge disubstitution ; Bridges (structures) ; Calixarenes ; Carbon dioxide ; Chemistry ; Conformational study ; Crystal structure ; Exact sciences and technology ; Organic chemistry ; Preparations and properties ; Synthesis (chemistry) ; Terminals ; Tetrahedrons ; X-ray crystallography ; X-rays</subject><ispartof>Tetrahedron, 2011-08, Vol.67 (31), p.5656-5662</ispartof><rights>2011</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-cf5600b35c1e16c9404c939ea0d0be8f01429645c269e15fb667ba9a8634e1653</citedby><cites>FETCH-LOGICAL-c360t-cf5600b35c1e16c9404c939ea0d0be8f01429645c269e15fb667ba9a8634e1653</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2011.05.087$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24303698$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Fischer, Conrad</creatorcontrib><creatorcontrib>Lin, Guisheng</creatorcontrib><creatorcontrib>Seichter, Wilhelm</creatorcontrib><creatorcontrib>Weber, Edwin</creatorcontrib><title>Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study</title><title>Tetrahedron</title><description>A series of calix[4]arenes bearing various substituents including alkyl,
p-bromobenzyl, carboxy and allyl at opposite methylene bridges has been synthesized via successive metallation followed by nucleophilic substitution. In a first step, mono-lithiated calix[4]arenes react with terminal bromoalkanes to give 2-alkylated calix[4]arenes or with CO
2 the respective calixarene-2-carboxylic acid in good yields. A second lithiation step of the monosubstituted products with subsequent attachment of both polar and non-polar substituents yields several new diametrally bridge-disubstituted calix[4]arenes. 2D-NMR measurements establish the disubstituted calixarenes to predominantly adopt the 1,2-
alternate conformation in solution. First examples of X-ray crystal structures of the new type of disubstituted calix[4]arenes are described featuring the calix[4]arene also in the rare 1,2-
alternate conformation.
[Display omitted]</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Allyl compounds</subject><subject>Attachment</subject><subject>Bridge disubstitution</subject><subject>Bridges (structures)</subject><subject>Calixarenes</subject><subject>Carbon dioxide</subject><subject>Chemistry</subject><subject>Conformational study</subject><subject>Crystal structure</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Synthesis (chemistry)</subject><subject>Terminals</subject><subject>Tetrahedrons</subject><subject>X-ray crystallography</subject><subject>X-rays</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kMFO3DAQhq2qSGyBB-DmSyUuSceJ7d2oJ0CFIiH1AJyqypo4k-JVSBaPs3TfHqNFHHua0ej7ZzSfEKcKSgXKfluXiVJZgVIlmBJWy09iobTVhdHKfhYLAA2FhgoOxRfmNUAmq3ohHi9i6P5S0QWeW04hzYk66XEI_37rPxhpJJZTmzCMeb4NKFGO9CI3kTYYMYUtyTjlUCnvdmN6JA4scewkpzj7NEcccjt3u2Nx0OPAdPJej8TD1Y_7y5_F7a_rm8vz28LXFlLhe2MB2tp4Rcr6RoP2Td0QQgctrXpQumqsNr6yDSnTt9YuW2xwZWudA6Y-Emf7vZs4Pc_EyT0F9jQMONI0s1NLre1SG7AZVXvUx4k5Uu82MTxh3DkF7s2qW7ts1b1ZdWBctpozX9_XI2dLfcTRB_4IVrqG2jarzH3fc5R_3QaKjn2g0VMXIvnkuin858or8ISN4g</recordid><startdate>20110805</startdate><enddate>20110805</enddate><creator>Fischer, Conrad</creator><creator>Lin, Guisheng</creator><creator>Seichter, Wilhelm</creator><creator>Weber, Edwin</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110805</creationdate><title>Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study</title><author>Fischer, Conrad ; Lin, Guisheng ; Seichter, Wilhelm ; Weber, Edwin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-cf5600b35c1e16c9404c939ea0d0be8f01429645c269e15fb667ba9a8634e1653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Allyl compounds</topic><topic>Attachment</topic><topic>Bridge disubstitution</topic><topic>Bridges (structures)</topic><topic>Calixarenes</topic><topic>Carbon dioxide</topic><topic>Chemistry</topic><topic>Conformational study</topic><topic>Crystal structure</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Synthesis (chemistry)</topic><topic>Terminals</topic><topic>Tetrahedrons</topic><topic>X-ray crystallography</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fischer, Conrad</creatorcontrib><creatorcontrib>Lin, Guisheng</creatorcontrib><creatorcontrib>Seichter, Wilhelm</creatorcontrib><creatorcontrib>Weber, Edwin</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</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>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fischer, Conrad</au><au>Lin, Guisheng</au><au>Seichter, Wilhelm</au><au>Weber, Edwin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study</atitle><jtitle>Tetrahedron</jtitle><date>2011-08-05</date><risdate>2011</risdate><volume>67</volume><issue>31</issue><spage>5656</spage><epage>5662</epage><pages>5656-5662</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A series of calix[4]arenes bearing various substituents including alkyl,
p-bromobenzyl, carboxy and allyl at opposite methylene bridges has been synthesized via successive metallation followed by nucleophilic substitution. In a first step, mono-lithiated calix[4]arenes react with terminal bromoalkanes to give 2-alkylated calix[4]arenes or with CO
2 the respective calixarene-2-carboxylic acid in good yields. A second lithiation step of the monosubstituted products with subsequent attachment of both polar and non-polar substituents yields several new diametrally bridge-disubstituted calix[4]arenes. 2D-NMR measurements establish the disubstituted calixarenes to predominantly adopt the 1,2-
alternate conformation in solution. First examples of X-ray crystal structures of the new type of disubstituted calix[4]arenes are described featuring the calix[4]arene also in the rare 1,2-
alternate conformation.
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| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Allyl compounds Attachment Bridge disubstitution Bridges (structures) Calixarenes Carbon dioxide Chemistry Conformational study Crystal structure Exact sciences and technology Organic chemistry Preparations and properties Synthesis (chemistry) Terminals Tetrahedrons X-ray crystallography X-rays |
| title | Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study |
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