Synthesis and conformational study of the first triply bridged calix[6]azatubes.
Identifieur interne : 000296 ( PubMed/Checkpoint ); précédent : 000295; suivant : 000297Synthesis and conformational study of the first triply bridged calix[6]azatubes.
Auteurs : Stéphane Le Gac [France] ; Xianshun Zeng ; Olivia Reinaud ; Ivan JabinSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2005.
Abstract
[reaction: see text] The first C(3)(v)- and D(3)(h)-symmetrical triply bridged calix[6]azatubes were prepared in good yields from the known 1,3,5-tris-methylated calix[6]arene through an efficient [1 + 1] macrocyclization reaction. A remarkably regioselective hexa ipso-nitration reaction led to a calix[6]azatube substituted at the wide rim in alternate position by tBu and nitro groups. A (1)H NMR study showed that, whereas the parent bis-calix[6]arenes self-include their methoxy groups, thereby closing their inner tube, the nitro-substituted calix[6]azatube undergoes a conformational change with the expulsion of the methoxy groups, hence presenting a three-dimensional structure open for host-guest applications.
DOI: 10.1021/jo048137l
PubMed: 15704952
Affiliations:
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A remarkably regioselective hexa ipso-nitration reaction led to a calix[6]azatube substituted at the wide rim in alternate position by tBu and nitro groups. A (1)H NMR study showed that, whereas the parent bis-calix[6]arenes self-include their methoxy groups, thereby closing their inner tube, the nitro-substituted calix[6]azatube undergoes a conformational change with the expulsion of the methoxy groups, hence presenting a three-dimensional structure open for host-guest applications.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">15704952</PMID><DateCreated><Year>2005</Year><Month>2</Month><Day>11</Day></DateCreated><DateCompleted><Year>2005</Year><Month>05</Month><Day>11</Day></DateCompleted><DateRevised><Year>2005</Year><Month>2</Month><Day>11</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-3263</ISSN><JournalIssue CitedMedium="Print"><Volume>70</Volume><Issue>4</Issue><PubDate><Year>2005</Year><Month>Feb</Month><Day>18</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Synthesis and conformational study of the first triply bridged calix[6]azatubes.</ArticleTitle><Pagination><MedlinePgn>1204-10</MedlinePgn></Pagination><Abstract><AbstractText>[reaction: see text] The first C(3)(v)- and D(3)(h)-symmetrical triply bridged calix[6]azatubes were prepared in good yields from the known 1,3,5-tris-methylated calix[6]arene through an efficient [1 + 1] macrocyclization reaction. A remarkably regioselective hexa ipso-nitration reaction led to a calix[6]azatube substituted at the wide rim in alternate position by tBu and nitro groups. A (1)H NMR study showed that, whereas the parent bis-calix[6]arenes self-include their methoxy groups, thereby closing their inner tube, the nitro-substituted calix[6]azatube undergoes a conformational change with the expulsion of the methoxy groups, hence presenting a three-dimensional structure open for host-guest applications.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Le Gac</LastName><ForeName>Stéphane</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Faculté des Sciences et Techniques, URCOM, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zeng</LastName><ForeName>Xianshun</ForeName><Initials>X</Initials></Author><Author ValidYN="Y"><LastName>Reinaud</LastName><ForeName>Olivia</ForeName><Initials>O</Initials></Author><Author ValidYN="Y"><LastName>Jabin</LastName><ForeName>Ivan</ForeName><Initials>I</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2005</Year><Month>2</Month><Day>12</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2005</Year><Month>2</Month><Day>12</Day><Hour>9</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2005</Year><Month>2</Month><Day>12</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">15704952</ArticleId><ArticleId IdType="doi">10.1021/jo048137l</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name><name sortKey="Reinaud, Olivia" sort="Reinaud, Olivia" uniqKey="Reinaud O" first="Olivia" last="Reinaud">Olivia Reinaud</name><name sortKey="Zeng, Xianshun" sort="Zeng, Xianshun" uniqKey="Zeng X" first="Xianshun" last="Zeng">Xianshun Zeng</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Le Gac, Stephane" sort="Le Gac, Stephane" uniqKey="Le Gac S" first="Stéphane" last="Le Gac">Stéphane Le Gac</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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