{"@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/1363670320726430336.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1002/hlca.19830660627"}},{"identifier":{"@type":"URI","@value":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.19830660627"}},{"identifier":{"@type":"URI","@value":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.19830660627"}}],"dc:title":[{"@value":"The Preparation of Optically Pure 7‐Oxabicyclo [2.2.1]hept‐2‐ene Derivatives. The CD Spectrum of (+)‐(1<i>R</i>)‐7‐Oxabicyclo [2.2.1]hept‐5‐en‐2‐one"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:title>Abstract</jats:title><jats:p>(−)‐1‐Camphanoyloxyacrylonitrile (=(−)‐1‐cyanovinyl camphanate; <jats:bold>1</jats:bold>) obtained from the commercially available (−)‐camphanoyl chloride and 2‐oxo‐propiononitrile added to furan at 20° in the presence of Cu (BF<jats:sub>4</jats:sub>)<jats:sub>2</jats:sub> · 6H<jats:sub>2</jats:sub>O or ZnI<jats:sub>2</jats:sub> and gave a mixture of 2‐cyano‐7‐oxabicyclo [2.2.1]hept‐5‐en‐2‐yl camphanates (<jats:bold>2–5</jats:bold>) from which isomer <jats:bold>5</jats:bold> could be obtained pure by crystallization. The latter was transformed into (+)‐(1<jats:italic>R</jats:italic>)‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐one (<jats:bold>6</jats:bold>) in high yield and optical purity. Adducts <jats:bold>2–4</jats:bold> were recycled into <jats:bold>1</jats:bold>+furan by heating in toluene, and (−)‐camphanic acid was recovered after saponification of <jats:bold>5</jats:bold>. The absolute configuration of <jats:bold>6</jats:bold> was deduced from its <jats:bold>CD</jats:bold> spectrum which showed two 1200‐cm<jats:sub>−1</jats:sub> <jats:italic>Franck</jats:italic>‐<jats:italic>Condon</jats:italic> series for its n→π<jats:inline-graphic xmlns:xlink=\"http://www.w3.org/1999/xlink\" xlink:href=\"graphic/tex2gif-stack-1.gif\" xlink:title=\"urn:x-wiley:0018019X:media:HLCA19830660627:tex2gif-stack-1\"/> transition.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1383670320726430336","@type":"Researcher","foaf:name":[{"@value":"Eric Vieira"}]},{"@id":"https://cir.nii.ac.jp/crid/1383670320726430337","@type":"Researcher","foaf:name":[{"@value":"Pierre Vogel"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"0018019X"},{"@type":"EISSN","@value":"15222675"}],"prism:publicationName":[{"@value":"Helvetica Chimica Acta"}],"dc:publisher":[{"@value":"Wiley"}],"prism:publicationDate":"1983-09-21","prism:volume":"66","prism:number":"6","prism:startingPage":"1865","prism:endingPage":"1871"},"reviewed":"false","dc:rights":["http://onlinelibrary.wiley.com/termsAndConditions#vor"],"url":[{"@id":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.19830660627"},{"@id":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.19830660627"}],"createdAt":"2004-12-28","modifiedAt":"2023-10-19","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360283694078976640","@type":"Article","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Preparatively Useful Method for the Synthesis of Diels-Alder Adducts between Furan and Methyl Acrylate"}]},{"@id":"https://cir.nii.ac.jp/crid/1360580232147247360","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@value":"Synthesis of <i>o</i>‐Bis(3‐indolyl)arenes under Brønsted Acid Catalysis: Carbonyl Compounds as Sources of Aryl Groups"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1002/hlca.19830660627"},{"@type":"CROSSREF","@value":"10.1246/bcsj.57.3339_references_DOI_TMppDyEzxrjfmROITYS4xtcU9jw"},{"@type":"CROSSREF","@value":"10.1002/adsc.202201340_references_DOI_TMppDyEzxrjfmROITYS4xtcU9jw"}]}