Diisophorone and related compounds. Part 18 ring contraction in diisophorone by the Favorski reaction
Identifieur interne : 002330 ( Main/Exploration ); précédent : 002329; suivant : 002331Diisophorone and related compounds. Part 18 ring contraction in diisophorone by the Favorski reaction
Auteurs : Frederick Kurzer [Royaume-Uni] ; Jayantilal N. Patel [Royaume-Uni]Source :
- Monatshefte für Chemie / Chemical Monthly [ 0026-9247 ] ; 1987-12-01.
English descriptors
- KwdEn :
- Teeft :
- Academic press, Alkaline hydrolysis, Aluminium, Anhydride, Anhydride formation, Anhydrous ether, Carbon skeleton, Chem, Chemical shift, Chim france, Cme2, Cooh, Coome, Crude product, Crystallisation, Diazomethane, Dicarboxylic acid, Diisophorone, Diisophorones, Electron impact, Ester, Ethanol, Ether, Ethereal diazomethane, Filtrate, Fragmentation patterns, Glacial acetic acid, Half volume, Higher field, Hydride, Hydriodic acid, Hydrochloric, Hydrochloric acid, Hydroxide, Individual compounds, Kurzer, Light petroleum, Lithium, Lithium aluminium hydride, Lower field, Magn reson, Mass spectra, Massive prisms, Methyl ester, Monatsh, Monatsh chem, Mult, Patel, Petroleum, Prism, Reagent, Reflux, Rooc cooh, Room temperature, Sodium carbonate, Sodium hydroxide, Spontaneous evaporation, Standard conditions, Substitution pattern.
Abstract
Abstract: The action of strong alkalis or alkoxides on 4,8-dibromo-1-carboxydiisophor-2(7)-en-3-one produces 1,3-dicarboxyneodiisophora-2,7-diene (or its esters) by a ring-contraction of theFavorski-type; the products are derivatives of tricyclo[6.3.1.02,6]dodecane. Hydriodic acid converts the dienedioic acid by partial saturation of the conjugated 2,7-diene system into the 2(7)-mono-olefinic dioic acid; the carboxyl groups of both series of compounds undergo esterification, anhydride formation and reduction in the normal manner. The13C nmr spectra of the novel ring-contracted compounds are interpreted, chiefly by reference to those of their diisophorone-precursors, as are their fragmentation patterns under electron impact.
Zusammenfassung: 4,8-Dibromdiisophor-2(7)-en-3-on-1-carbonsäure wird von Alkalien oder Natriumalkoholaten durch eineFavorski-artige Ringverengung in Neodiisophora-2,7-dien-1,3-dicarbonsäure (oder deren Ester) verwandelt; die Reaktionsprodukte sind Abkömmlinge des Tricyclo[6.3.1.02,6] dodekans. Partielle Sättigung der konjugierten Doppelbindungen mittels Iodwasserstoffsäure ergibt die entsprechenden 2(7)-Mono-olefine. Veresterung, Anhydridbildung und Reduktion der Carboxylgruppen beider Verbindungsreihen verlaufen normal. Die13C-Kernresonanz-und Massenspektren der neuen Strukturen werden auf Grund bekannter Spektren der verwandten Diisophoron-Reihe gedeutet.
Url:
DOI: 10.1007/BF00810642
Affiliations:
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Patel</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:0537684C853D4DE0DA2A1D7B72E92F227B627E5B</idno><date when="1987" year="1987">1987</date><idno type="doi">10.1007/BF00810642</idno><idno type="url">https://api.istex.fr/ark:/67375/1BB-FD7LC0SX-9/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">001485</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">001485</idno><idno type="wicri:Area/Istex/Curation">001485</idno><idno type="wicri:Area/Istex/Checkpoint">001032</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">001032</idno><idno type="wicri:doubleKey">0026-9247:1987:Kurzer F:diisophorone:and:related</idno><idno type="wicri:Area/Main/Merge">002441</idno><idno type="wicri:Area/Main/Curation">002330</idno><idno type="wicri:Area/Main/Exploration">002330</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Diisophorone and related compounds. Part 18 ring contraction in diisophorone by the Favorski reaction</title><author><name sortKey="Kurzer, Frederick" sort="Kurzer, Frederick" uniqKey="Kurzer F" first="Frederick" last="Kurzer">Frederick Kurzer</name><affiliation wicri:level="4"><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Royal Free Hospital School of Medicine, University of London, London</wicri:regionArea><placeName><settlement type="city">Londres</settlement><region type="country">Angleterre</region><region type="région" nuts="1">Grand Londres</region></placeName><orgName type="university">Université de Londres</orgName></affiliation></author><author><name sortKey="Patel, Jayantilal N" sort="Patel, Jayantilal N" uniqKey="Patel J" first="Jayantilal N." last="Patel">Jayantilal N. Patel</name><affiliation wicri:level="4"><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Royal Free Hospital School of Medicine, University of London, London</wicri:regionArea><placeName><settlement type="city">Londres</settlement><region type="country">Angleterre</region><region type="région" nuts="1">Grand Londres</region></placeName><orgName type="university">Université de Londres</orgName></affiliation></author></analytic><monogr></monogr><series><title level="j">Monatshefte für Chemie / Chemical Monthly</title><title level="j" type="abbrev">Monatsh Chem</title><idno type="ISSN">0026-9247</idno><idno type="eISSN">1434-4475</idno><imprint><publisher>Springer-Verlag</publisher><pubPlace>Vienna</pubPlace><date type="published" when="1987-12-01">1987-12-01</date><biblScope unit="volume">118</biblScope><biblScope unit="issue">12</biblScope><biblScope unit="page" from="1363">1363</biblScope><biblScope unit="page" to="1381">1381</biblScope></imprint><idno type="ISSN">0026-9247</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0026-9247</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>4,8-Methano-1H-cyclopentacyclooctenes</term><term>Diisophorone, Favorski ring contraction thereof</term><term>Tricyclo[6,3,1,02,6]dodecanes</term><term>“Neodiisophorones”</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Academic press</term><term>Alkaline hydrolysis</term><term>Aluminium</term><term>Anhydride</term><term>Anhydride formation</term><term>Anhydrous ether</term><term>Carbon skeleton</term><term>Chem</term><term>Chemical shift</term><term>Chim france</term><term>Cme2</term><term>Cooh</term><term>Coome</term><term>Crude product</term><term>Crystallisation</term><term>Diazomethane</term><term>Dicarboxylic acid</term><term>Diisophorone</term><term>Diisophorones</term><term>Electron impact</term><term>Ester</term><term>Ethanol</term><term>Ether</term><term>Ethereal diazomethane</term><term>Filtrate</term><term>Fragmentation patterns</term><term>Glacial acetic acid</term><term>Half volume</term><term>Higher field</term><term>Hydride</term><term>Hydriodic acid</term><term>Hydrochloric</term><term>Hydrochloric acid</term><term>Hydroxide</term><term>Individual compounds</term><term>Kurzer</term><term>Light petroleum</term><term>Lithium</term><term>Lithium aluminium hydride</term><term>Lower field</term><term>Magn reson</term><term>Mass spectra</term><term>Massive prisms</term><term>Methyl ester</term><term>Monatsh</term><term>Monatsh chem</term><term>Mult</term><term>Patel</term><term>Petroleum</term><term>Prism</term><term>Reagent</term><term>Reflux</term><term>Rooc cooh</term><term>Room temperature</term><term>Sodium carbonate</term><term>Sodium hydroxide</term><term>Spontaneous evaporation</term><term>Standard conditions</term><term>Substitution pattern</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: The action of strong alkalis or alkoxides on 4,8-dibromo-1-carboxydiisophor-2(7)-en-3-one produces 1,3-dicarboxyneodiisophora-2,7-diene (or its esters) by a ring-contraction of theFavorski-type; the products are derivatives of tricyclo[6.3.1.02,6]dodecane. Hydriodic acid converts the dienedioic acid by partial saturation of the conjugated 2,7-diene system into the 2(7)-mono-olefinic dioic acid; the carboxyl groups of both series of compounds undergo esterification, anhydride formation and reduction in the normal manner. The13C nmr spectra of the novel ring-contracted compounds are interpreted, chiefly by reference to those of their diisophorone-precursors, as are their fragmentation patterns under electron impact.</div><div type="abstract" xml:lang="de">Zusammenfassung: 4,8-Dibromdiisophor-2(7)-en-3-on-1-carbonsäure wird von Alkalien oder Natriumalkoholaten durch eineFavorski-artige Ringverengung in Neodiisophora-2,7-dien-1,3-dicarbonsäure (oder deren Ester) verwandelt; die Reaktionsprodukte sind Abkömmlinge des Tricyclo[6.3.1.02,6] dodekans. Partielle Sättigung der konjugierten Doppelbindungen mittels Iodwasserstoffsäure ergibt die entsprechenden 2(7)-Mono-olefine. Veresterung, Anhydridbildung und Reduktion der Carboxylgruppen beider Verbindungsreihen verlaufen normal. Die13C-Kernresonanz-und Massenspektren der neuen Strukturen werden auf Grund bekannter Spektren der verwandten Diisophoron-Reihe gedeutet.</div></front></TEI><affiliations><list><country><li>Royaume-Uni</li></country><region><li>Angleterre</li><li>Grand Londres</li></region><settlement><li>Londres</li></settlement><orgName><li>Université de Londres</li></orgName></list><tree><country name="Royaume-Uni"><region name="Angleterre"><name sortKey="Kurzer, Frederick" sort="Kurzer, Frederick" uniqKey="Kurzer F" first="Frederick" last="Kurzer">Frederick Kurzer</name></region><name sortKey="Patel, Jayantilal N" sort="Patel, Jayantilal N" uniqKey="Patel J" first="Jayantilal N." last="Patel">Jayantilal N. Patel</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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