{"@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/1360004233131124608.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/acs.joc.7b02573"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b02573"}},{"identifier":{"@type":"PMID","@value":"29189006"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Contrasting C- and O-Atom Reactivities of Neutral Ketone and Enolate Forms of 3-Sulfonyloxyimino-2-methyl-1-phenyl-1-butanones"}],"description":[{"notation":[{"@value":"The mechanisms of intramolecular cyclization of 3-sulfonyloxyimino-2-methyl-1-phenyl-1-butanones (1) under basic (DABCO and t-BuOK) and acidic (AcOH and TFA) conditions were investigated by means of experimental and computational methods. The ketone, enol, and enolate forms of 1 can afford different intramolecular cyclization products (2, 3, 4), depending on the conditions. The results of the reaction of 1 under basic conditions suggest intermediacy of neutral enol (DABCO) and anionic enolate (t-BuOK), while the results under acidic conditions (AcOH and TFA) indicate involvement of neutral ketones, which exhibit reactivities arising from both the oxygen lone-pair electrons (O atom reactivity) and carbon σ-electrons (C atom reactivity). The neutral enol in DABCO afforded 2H-azirine 4. On the other hand, the products (isoxazole 2 and oxazole 3) generated from the ketone form and from the enolate form are the same, but the reaction mechanisms are apparently different. The results demonstrate ambident-like reactivity of neutral ketone in the 3-sulfonyloxyimino-2-methyl-1-phenyl-1-butanone system."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380004233131124609","@type":"Researcher","foaf:name":[{"@value":"Yingtang Ning"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1420845751141903232","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"60451853"},{"@type":"NRID","@value":"1000060451853"},{"@type":"NRID","@value":"9000014611528"}],"foaf:name":[{"@value":"Yuko Otani"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380004233131124608","@type":"Researcher","foaf:name":[{"@value":"Tomohiko Ohwada"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033, Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00223263"},{"@type":"EISSN","@value":"15206904"}],"prism:publicationName":[{"@value":"The Journal of Organic Chemistry"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2017-12-20","prism:volume":"83","prism:number":"1","prism:startingPage":"203","prism:endingPage":"219"},"reviewed":"false","url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b02573"}],"createdAt":"2017-11-30","modifiedAt":"2023-04-13","project":[{"@id":"https://cir.nii.ac.jp/crid/1040000781894063232","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"16H00822"},{"@type":"JGN","@value":"JP16H00822"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PUBLICLY-16H00822/"}],"notation":[{"@language":"ja","@value":"プロリン型人工アミノ酸をモジュールとするα－アミノ酸ペプチドの構造化効果"},{"@language":"en","@value":"Study of structure effect of proline-type non-natural amino acids incorporated in alpha-amino acid peptides"}]},{"@id":"https://cir.nii.ac.jp/crid/1040282256890454912","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"16K08157"},{"@type":"JGN","@value":"JP16K08157"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-16K08157/"}],"notation":[{"@language":"ja","@value":"α/β－ヘテロペプチドを基盤とした新規構造と機能の創出"},{"@language":"en","@value":"Generation of regular structure with function based on alpha/beta-heteropeptides"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360004233130978688","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Base-Induced Transformation of 2-Acyl-3-alkyl-2<i>H</i>-azirines to Oxazoles: Involvement of Deprotonation-Initiated Pathways"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004233229804800","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Origin of Regioselectivity in the Reactions of Nitronate and Enolate Ambident Anions"}]},{"@id":"https://cir.nii.ac.jp/crid/1360004233608640128","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Revisiting secondary interactions in neighboring group participation, exemplified by reactivity changes of iminylium intermediates"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011143997903232","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"The Chemistry of Transition Metals with Three-Membered Ring Heterocycles"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011144391660416","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Intermediates in the Paal-Knorr Synthesis of Furans"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011144512752768","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Chemical and Electrochemical Electron-Transfer Theory"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011144710262144","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Allylmagnesium Halides Do Not React Chemoselectively Because Reaction Rates Approach the Diffusion Limit"}]},{"@id":"https://cir.nii.ac.jp/crid/1360011144736523008","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Is the Beckmann Rearrangement a Concerted or Stepwise Reaction? 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