{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1362825894524581248.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/jccs.199100052"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fjccs.199100052"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/jccs.199100052"}}],"dc:title":[{"@value":"On the Discovery of Direct Ortho‐Magnesiation"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>Metalation of 2,4‐dicyanocubanecarboxamide (4) with lithium tetramethylpiperidide (LiTMP) followed by quenching with CO<jats:sub>2</jats:sub> is non‐regioselective and results in carboxylation at the 3 (→ 5) and 6 (→ 6 ) positions. However, when the reaction was repeated with LiTMP pre‐treated with more than 0.5 equivalent of MgBr<jats:sub>2</jats:sub>, only 6 was produced. This was shown to occur by direct, regiospecific ortho‐magnesiation by the bases BrMgTMP and MgTMP<jats:sub>2</jats:sub>. This initial observation of ortho‐magnesiation has opened the way to wide application of this new methodology, a valuable and useful complement to ortho‐lithiation.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1382825894524581248","@type":"Researcher","foaf:name":[{"@value":"Philip E. Eaton"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825894524581249","@type":"Researcher","foaf:name":[{"@value":"Yusheng Xiong"}]},{"@id":"https://cir.nii.ac.jp/crid/1380016870196284032","@type":"Researcher","foaf:name":[{"@value":"Chih‐Hung Lee"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00094536"},{"@type":"EISSN","@value":"21926549"}],"prism:publicationName":[{"@value":"Journal of the Chinese Chemical Society"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"1991-08","prism:volume":"38","prism:number":"4","prism:startingPage":"303","prism:endingPage":"306"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fjccs.199100052"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/jccs.199100052"}],"createdAt":"2015-06-04","modifiedAt":"2023-10-22","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050585493123883392","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"How to Set the “Chirality” of Polyhedral Small Molecule Hydrocarbons: Decoration and Editing of Cubane Skeleton"}]},{"@id":"https://cir.nii.ac.jp/crid/1050856660844282880","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Catalytic Asymmetric Synthesis of 2,6‐Disubstituted Cuneanes via Enantioselective Constitutional Isomerization of 1,4‐Disubstituted Cubanes"},{"@value":"Catalytic Asymmetric Synthesis of 2,6‐Disubstituted Cuneanes through Enantioselective Constitutional Isomerization of 1,4‐Disubstituted Cubanes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360298337126967808","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Directed Metalation of 1-Cuneanecarboxamide: Simple Route to 1,2-Disubstituted Cuneanes"}]},{"@id":"https://cir.nii.ac.jp/crid/1360298341430199424","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Chiral Auxiliary-Directed Site-Selective Deprotonation of the Cubane Skeleton"}]},{"@id":"https://cir.nii.ac.jp/crid/1360576121598039424","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Unmasking Inherent Chirality within the Cubane Skeleton"}]},{"@id":"https://cir.nii.ac.jp/crid/1360853567643792128","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation"}]},{"@id":"https://cir.nii.ac.jp/crid/1360865814731655936","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Decoration on Cubane with an Awareness of Chirality: Development of Substituted Cubane Syntheses"}]},{"@id":"https://cir.nii.ac.jp/crid/1361975842845956352","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Cubane Chirality via Substitution of a “Hidden” Regular Tetrahedron"}]},{"@id":"https://cir.nii.ac.jp/crid/2050588892112986880","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Studies for absolute configuration of chiral 2,6-cuneanedicarboxylic acid esters"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/jccs.199100052"},{"@type":"CROSSREF","@value":"10.1021/acs.orglett.2c03659_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1002/ejoc.202200567_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1246/cl.230101_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1002/ejoc.202300891_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1021/acs.orglett.0c01142_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1002/ijch.202100013_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1039/d0sc01909g_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1246/cl.220197_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"},{"@type":"CROSSREF","@value":"10.1055/a-2124-3823_references_DOI_WynsEdRbzUrf72Mao722a6XPyB1"}]}