Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols
Identifieur interne : 000680 ( Istex/Corpus ); précédent : 000679; suivant : 000681Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols
Auteurs : Pascal Pigeon ; A Cha Mamouni ; Jana Sikoraiova ; Stefan Marchalin ; Bernard DecroixSource :
- Tetrahedron [ 0040-4020 ] ; 2001.
English descriptors
Abstract
Hydroxylactam-alcohols 5a,b,d (isoindole series), under acidic treatment gave phthalimides 7a,b,d via a hydride shift induced by an intramolecular π-stacking (benzene–benzene or benzene–thiophene interaction) which did not occur in 10a (succinimide series).
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DOI: 10.1016/S0040-4020(01)00437-9
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Tel.: +33-02-32-74-43-95; fax: +33-02-32-74-43-91</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: bernard.decroix@univ-lehavre.fr</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="ISSN">0040-4020</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="2001">2001</date><biblScope unit="volume">57</biblScope><biblScope unit="issue">23</biblScope><biblScope unit="page" from="4939">4939</biblScope><biblScope unit="page" to="4943">4943</biblScope></imprint><idno type="ISSN">0040-4020</idno></series><idno type="istex">DB08E19006FBEEAF48ADD5A7D2D19E4C0B61EFEB</idno><idno type="DOI">10.1016/S0040-4020(01)00437-9</idno><idno type="PII">S0040-4020(01)00437-9</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4020</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>iminium salts</term><term>isoindole</term><term>oxazepines</term><term>polycyclic heterocyclic compounds</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Hydroxylactam-alcohols 5a,b,d (isoindole series), under acidic treatment gave phthalimides 7a,b,d via a hydride shift induced by an intramolecular π-stacking (benzene–benzene or benzene–thiophene interaction) which did not occur in 10a (succinimide series).</div></front></TEI><istex><corpusName>elsevier</corpusName><author><json:item><name>Pascal Pigeon</name><affiliations><json:string>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</json:string></affiliations></json:item><json:item><name>Aı̈cha Mamouni</name><affiliations><json:string>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</json:string></affiliations></json:item><json:item><name>Jana Sikoraiova</name><affiliations><json:string>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic</json:string></affiliations></json:item><json:item><name>Stefan Marchalin</name><affiliations><json:string>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic</json:string></affiliations></json:item><json:item><name>Bernard Decroix</name><affiliations><json:string>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</json:string><json:string>Corresponding author. 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Tel.: +33-02-32-74-43-95; fax: +33-02-32-74-43-91</affiliation></author></analytic><monogr><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="pISSN">0040-4020</idno><idno type="PII">S0040-4020(00)X1106-4</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="2001"></date><biblScope unit="volume">57</biblScope><biblScope unit="issue">23</biblScope><biblScope unit="page" from="4939">4939</biblScope><biblScope unit="page" to="4943">4943</biblScope></imprint></monogr><idno type="istex">DB08E19006FBEEAF48ADD5A7D2D19E4C0B61EFEB</idno><idno type="DOI">10.1016/S0040-4020(01)00437-9</idno><idno type="PII">S0040-4020(01)00437-9</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>2001</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>Hydroxylactam-alcohols 5a,b,d (isoindole series), under acidic treatment gave phthalimides 7a,b,d via a hydride shift induced by an intramolecular π-stacking (benzene–benzene or benzene–thiophene interaction) which did not occur in 10a (succinimide series).</p></abstract><abstract style="graphical"><p>The acid treatment of 5a,b,d and 10a leading to a hydride shift only for 6a,b,d is discussed.gr1</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>Keywords</head><item><term>iminium salts</term></item><item><term>isoindole</term></item><item><term>oxazepines</term></item><item><term>polycyclic heterocyclic compounds</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2001-04-18">Modified</change><change when="2001">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><original>false</original><mimetype>text/plain</mimetype><extension>txt</extension><uri>https://api.istex.fr/document/DB08E19006FBEEAF48ADD5A7D2D19E4C0B61EFEB/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: ce:floats; body; tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"><istex:entity SYSTEM="gr1" NDATA="IMAGE" name="gr1"></istex:entity><istex:entity SYSTEM="sc1" NDATA="IMAGE" name="sc1"></istex:entity><istex:entity SYSTEM="sc2" NDATA="IMAGE" name="sc2"></istex:entity><istex:entity SYSTEM="sc3" NDATA="IMAGE" name="sc3"></istex:entity><istex:entity SYSTEM="sc4" NDATA="IMAGE" name="sc4"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla" xml:lang="en"><item-info><jid>TET</jid><aid>9319</aid><ce:pii>S0040-4020(01)00437-9</ce:pii><ce:doi>10.1016/S0040-4020(01)00437-9</ce:doi><ce:copyright type="full-transfer" year="2001">Elsevier Science Ltd</ce:copyright></item-info><head><ce:title>Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols</ce:title><ce:author-group><ce:author><ce:given-name>Pascal</ce:given-name><ce:surname>Pigeon</ce:surname><ce:cross-ref refid="AFF1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Aı̈cha</ce:given-name><ce:surname>Mamouni</ce:surname><ce:cross-ref refid="AFF1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Jana</ce:given-name><ce:surname>Sikoraiova</ce:surname><ce:cross-ref refid="AFF2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Stefan</ce:given-name><ce:surname>Marchalin</ce:surname><ce:cross-ref refid="AFF2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Bernard</ce:given-name><ce:surname>Decroix</ce:surname><ce:cross-ref refid="AFF1"><ce:sup>a</ce:sup></ce:cross-ref><ce:cross-ref refid="COR1"><ce:sup>∗</ce:sup></ce:cross-ref><ce:e-address>bernard.decroix@univ-lehavre.fr</ce:e-address></ce:author><ce:affiliation id="AFF1"><ce:label>a</ce:label><ce:textfn>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</ce:textfn></ce:affiliation><ce:affiliation id="AFF2"><ce:label>b</ce:label><ce:textfn>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic</ce:textfn></ce:affiliation><ce:correspondence id="COR1"><ce:label>∗</ce:label><ce:text>Corresponding author. Tel.: +33-02-32-74-43-95; fax: +33-02-32-74-43-91</ce:text></ce:correspondence></ce:author-group><ce:date-received day="16" month="2" year="2001"></ce:date-received><ce:date-revised day="18" month="4" year="2001"></ce:date-revised><ce:date-accepted day="20" month="4" year="2001"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>Hydroxylactam-alcohols <ce:bold>5a</ce:bold>,<ce:bold>b</ce:bold>,<ce:bold>d</ce:bold> (isoindole series), under acidic treatment gave phthalimides <ce:bold>7a</ce:bold>,<ce:bold>b</ce:bold>,<ce:bold>d</ce:bold> via a hydride shift induced by an intramolecular π-stacking (benzene–benzene or benzene–thiophene interaction) which did not occur in <ce:bold>10a</ce:bold> (succinimide series).</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>The acid treatment of <ce:bold>5a</ce:bold>,<ce:bold>b</ce:bold>,<ce:bold>d</ce:bold> and <ce:bold>10a</ce:bold> leading to a hydride shift only for <ce:bold>6a</ce:bold>,<ce:bold>b</ce:bold>,<ce:bold>d</ce:bold> is discussed.</ce:simple-para></ce:abstract-sec><ce:figure><ce:link locator="gr1"></ce:link></ce:figure></ce:abstract><ce:keywords class="keyword" xml:lang="en"><ce:section-title>Keywords</ce:section-title><ce:keyword><ce:text>iminium salts</ce:text></ce:keyword><ce:keyword><ce:text>isoindole</ce:text></ce:keyword><ce:keyword><ce:text>oxazepines</ce:text></ce:keyword><ce:keyword><ce:text>polycyclic heterocyclic compounds</ce:text></ce:keyword></ce:keywords></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols</title></titleInfo><titleInfo type="alternative" lang="en" contentType="CDATA"><title>Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols</title></titleInfo><name type="personal"><namePart type="given">Pascal</namePart><namePart type="family">Pigeon</namePart><affiliation>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Aı̈cha</namePart><namePart type="family">Mamouni</namePart><affiliation>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jana</namePart><namePart type="family">Sikoraiova</namePart><affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Stefan</namePart><namePart type="family">Marchalin</namePart><affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bernard</namePart><namePart type="family">Decroix</namePart><affiliation>Laboratoire de Chimie, Faculté des Sciences et des Techniques de l'Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France</affiliation><affiliation>Corresponding author. Tel.: +33-02-32-74-43-95; fax: +33-02-32-74-43-91</affiliation><affiliation>E-mail: bernard.decroix@univ-lehavre.fr</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article"></genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">2001</dateIssued><dateModified encoding="w3cdtf">2001-04-18</dateModified><copyrightDate encoding="w3cdtf">2001</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract lang="en">Hydroxylactam-alcohols 5a,b,d (isoindole series), under acidic treatment gave phthalimides 7a,b,d via a hydride shift induced by an intramolecular π-stacking (benzene–benzene or benzene–thiophene interaction) which did not occur in 10a (succinimide series).</abstract><abstract type="graphical">The acid treatment of 5a,b,d and 10a leading to a hydride shift only for 6a,b,d is discussed.gr1 </abstract><note type="content">Scheme 1: </note><note type="content">Scheme 2: </note><note type="content">Scheme 3: </note><note type="content">Scheme 4: </note><subject lang="en"><genre>Keywords</genre><topic>iminium salts</topic><topic>isoindole</topic><topic>oxazepines</topic><topic>polycyclic heterocyclic compounds</topic></subject><relatedItem type="host"><titleInfo><title>Tetrahedron</title></titleInfo><titleInfo type="abbreviated"><title>TET</title></titleInfo><genre type="journal">journal</genre><originInfo><dateIssued encoding="w3cdtf">20010604</dateIssued></originInfo><identifier type="ISSN">0040-4020</identifier><identifier type="PII">S0040-4020(00)X1106-4</identifier><part><date>20010604</date><detail type="volume"><number>57</number><caption>vol.</caption></detail><detail type="issue"><number>23</number><caption>no.</caption></detail><extent unit="issue pages"><start>4801</start><end>5026</end></extent><extent unit="pages"><start>4939</start><end>4943</end></extent></part></relatedItem><identifier type="istex">DB08E19006FBEEAF48ADD5A7D2D19E4C0B61EFEB</identifier><identifier type="DOI">10.1016/S0040-4020(01)00437-9</identifier><identifier type="PII">S0040-4020(01)00437-9</identifier><accessCondition type="use and reproduction" contentType="copyright">©2001 Elsevier Science Ltd</accessCondition><recordInfo><recordContentSource>ELSEVIER</recordContentSource><recordOrigin>Elsevier Science Ltd, ©2001</recordOrigin></recordInfo></mods></metadata><enrichments><istex:catWosTEI uri="https://api.istex.fr/document/DB08E19006FBEEAF48ADD5A7D2D19E4C0B61EFEB/enrichments/catWos"><teiHeader><profileDesc><textClass><classCode scheme="WOS">CHEMISTRY, ORGANIC</classCode></textClass></profileDesc></teiHeader></istex:catWosTEI></enrichments><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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