Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides
Identifieur interne : 000325 ( Istex/Corpus ); précédent : 000324; suivant : 000326Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides
Auteurs : Lucjan Strekowski ; Steven Patterson ; Marek T. Cegla ; Roman L. Wydra ; Agnieszka Czarny ; Donald B. HardenSource :
- Tetrahedron Letters [ 0040-4039 ] ; 1989.
English descriptors
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Abstract
Abstract: Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.
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DOI: 10.1016/S0040-4039(01)93740-2
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<front><div type="abstract" xml:lang="en">Abstract: Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</div>
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<abstract xml:lang="en"><p>Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</p>
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<head><ce:title>Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides</ce:title>
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<ce:note-para>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</ce:note-para>
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<ce:abstract><ce:section-title>Abstract</ce:section-title>
<ce:abstract-sec><ce:simple-para>Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the <ce:italic>ortho</ce:italic>
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<ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>Lithiation with to give secondary enamines after quenching with H<ce:inf>2</ce:inf>
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<affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation>
<description>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</description>
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<name type="personal"><namePart type="given">Donald B.</namePart>
<namePart type="family">Harden</namePart>
<affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation>
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<dateIssued encoding="w3cdtf">1989</dateIssued>
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<language><languageTerm type="code" authority="iso639-2b">eng</languageTerm>
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<abstract lang="en">Abstract: Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</abstract>
<abstract type="graphical">Lithiation with to give secondary enamines after quenching with H2Ogr1 </abstract>
<relatedItem type="host"><titleInfo><title>Tetrahedron Letters</title>
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<originInfo><publisher>ELSEVIER</publisher>
<dateIssued encoding="w3cdtf">1989</dateIssued>
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<identifier type="ISSN">0040-4039</identifier>
<identifier type="PII">S0040-4039(00)X0753-8</identifier>
<part><date>1989</date>
<detail type="volume"><number>30</number>
<caption>vol.</caption>
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<detail type="issue"><number>39</number>
<caption>no.</caption>
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<extent unit="issue-pages"><start>5177</start>
<end>5376</end>
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<extent unit="pages"><start>5197</start>
<end>5200</end>
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<identifier type="DOI">10.1016/S0040-4039(01)93740-2</identifier>
<identifier type="PII">S0040-4039(01)93740-2</identifier>
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