Reaction of dianions of acyclic β-enamino ketones with electrophiles. 8. Synthesis of trialkylsilylenaminones and α′-silylated β-diketones
Identifieur interne : 000436 ( Istex/Corpus ); précédent : 000435; suivant : 000437Reaction of dianions of acyclic β-enamino ketones with electrophiles. 8. Synthesis of trialkylsilylenaminones and α′-silylated β-diketones
Auteurs : Giuseppe Bartoli ; Marcella Bosco ; Renato Dalpozzo ; Antonio De Nino ; Emma Iantorno ; Antonio Tagarelli ; Gianni PalmieriSource :
- Tetrahedron [ 0040-4020 ] ; 1996.
English descriptors
- KwdEn :
- Acyclic ketones, Ammonium chloride, Anal, Anal calcd, Bartoli, Bosco, Butme2, Calcd, Ch2si, Chem, Chromatographic separation, Cimarelli, Corresponding products, Dalpozzo, Dianion, Dianions, Enaminones, Hexane ethyl acetate, Hydrochloric acid, Ketone, Me2si, Me3c, Me3si, Other hand, Palmieri, Perkin trans, Reaction mixture, Room temperature, Silylated, Sodium sulphate, Tetrahedron, Twofold amount, Vmax.
- Teeft :
- Acyclic ketones, Ammonium chloride, Anal, Anal calcd, Bartoli, Bosco, Butme2, Calcd, Ch2si, Chem, Chromatographic separation, Cimarelli, Corresponding products, Dalpozzo, Dianion, Dianions, Enaminones, Hexane ethyl acetate, Hydrochloric acid, Ketone, Me2si, Me3c, Me3si, Other hand, Palmieri, Perkin trans, Reaction mixture, Room temperature, Silylated, Sodium sulphate, Tetrahedron, Twofold amount, Vmax.
Abstract
Abstract: α′- and γ-Dianions of β-(monoalkylamino) α,β-unsaturated ketones react with trialkylchlorosilanes leading to α′- and γ-trialkylsilylenaminones. Conversely from trimethylchlorosilane, the reaction between dianions of 3-(N-isopropylamino)-1-arylbut-2-en-1-ones and t-butyldimethylchlorosilane or triisopropylchlorosilane leads to the corresponding 4-trialkylsilyl derivatives. An explanation of these findings is reported. Hydrolysis of these compounds affords the until now unknown α′ silylated β-diketones.
Url:
DOI: 10.1016/0040-4020(96)00468-1
Links to Exploration step
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<front><div type="abstract" xml:lang="en">Abstract: α′- and γ-Dianions of β-(monoalkylamino) α,β-unsaturated ketones react with trialkylchlorosilanes leading to α′- and γ-trialkylsilylenaminones. Conversely from trimethylchlorosilane, the reaction between dianions of 3-(N-isopropylamino)-1-arylbut-2-en-1-ones and t-butyldimethylchlorosilane or triisopropylchlorosilane leads to the corresponding 4-trialkylsilyl derivatives. An explanation of these findings is reported. Hydrolysis of these compounds affords the until now unknown α′ silylated β-diketones.</div>
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<ce:note-para>Part 7: see ref. 7</ce:note-para>
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<ce:title>Reaction of dianions of acyclic β-enamino ketones with electrophiles. 8. Synthesis of trialkylsilylenaminones and α′-silylated β-diketones</ce:title>
<ce:author-group><ce:author><ce:given-name>Giuseppe</ce:given-name>
<ce:surname>Bartoli</ce:surname>
</ce:author>
<ce:author><ce:given-name>Marcella</ce:given-name>
<ce:surname>Bosco</ce:surname>
</ce:author>
<ce:affiliation><ce:textfn>Dipartimento di Chimica Organica ‘A. Mangini’, viale Risorgimento 4, I-40136 Bologna, Italy</ce:textfn>
</ce:affiliation>
</ce:author-group>
<ce:author-group><ce:author><ce:given-name>Renato</ce:given-name>
<ce:surname>Dalpozzo</ce:surname>
<ce:ranking><ce:sup>∗</ce:sup>
</ce:ranking>
</ce:author>
<ce:author><ce:given-name>Antonio</ce:given-name>
<ce:surname>De Nino</ce:surname>
</ce:author>
<ce:author><ce:given-name>Emma</ce:given-name>
<ce:surname>Iantorno</ce:surname>
</ce:author>
<ce:author><ce:given-name>Antonio</ce:given-name>
<ce:surname>Tagarelli</ce:surname>
</ce:author>
<ce:affiliation><ce:textfn>Dipartimento di Chimica, Università della Calabria, I-87030 Arcavacata di Rende (Cosenza), Italy</ce:textfn>
</ce:affiliation>
</ce:author-group>
<ce:author-group><ce:author><ce:given-name>Gianni</ce:given-name>
<ce:surname>Palmieri</ce:surname>
</ce:author>
<ce:affiliation><ce:textfn>Dipartimento di Scienze Chimiche, via S. Agostino I, I-62032 Camerino (Macerata), Italy</ce:textfn>
</ce:affiliation>
</ce:author-group>
<ce:date-received day="11" month="4" year="1996"></ce:date-received>
<ce:date-revised day="15" month="5" year="1996"></ce:date-revised>
<ce:date-accepted day="16" month="5" year="1996"></ce:date-accepted>
<ce:abstract><ce:section-title>Abstract</ce:section-title>
<ce:abstract-sec><ce:simple-para>α′- and γ-Dianions of β-(monoalkylamino) α,β-unsaturated ketones react with trialkylchlorosilanes leading to α′- and γ-trialkylsilylenaminones. Conversely from trimethylchlorosilane, the reaction between dianions of 3-(<ce:italic>N</ce:italic>
-isopropylamino)-1-arylbut-2-en-1-ones and <ce:italic>t</ce:italic>
-butyldimethylchlorosilane or triisopropylchlorosilane leads to the corresponding 4-trialkylsilyl derivatives. An explanation of these findings is reported. Hydrolysis of these compounds affords the until now unknown α′ silylated β-diketones.</ce:simple-para>
</ce:abstract-sec>
</ce:abstract>
<ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>α′- and γ-Dianions of β-(monoalkylamino) α, β-unsaturated ketones react with trialkylchlorosilanes leading to α′- and γ-trialkylsilylenaminones. Hydrolysis of these compounds affords the until now unknown α′ silylated β-diketones.</ce:simple-para>
</ce:abstract-sec>
<ce:figure><ce:link locator="gr1"></ce:link>
</ce:figure>
</ce:abstract>
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<titleInfo type="alternative" contentType="CDATA"><title>Reaction of dianions of acyclic β-enamino ketones with electrophiles. 8. Synthesis of trialkylsilylenaminones and α′-silylated β-diketones</title>
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<name type="personal"><namePart type="given">Giuseppe</namePart>
<namePart type="family">Bartoli</namePart>
<affiliation>Dipartimento di Chimica Organica ‘A. Mangini’, viale Risorgimento 4, I-40136 Bologna, Italy</affiliation>
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<name type="personal"><namePart type="given">Marcella</namePart>
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<name type="personal"><namePart type="given">Renato</namePart>
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<name type="personal"><namePart type="given">Antonio</namePart>
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<name type="personal"><namePart type="given">Emma</namePart>
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<name type="personal"><namePart type="given">Antonio</namePart>
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<role><roleTerm type="text">author</roleTerm>
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<name type="personal"><namePart type="given">Gianni</namePart>
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<abstract lang="en">Abstract: α′- and γ-Dianions of β-(monoalkylamino) α,β-unsaturated ketones react with trialkylchlorosilanes leading to α′- and γ-trialkylsilylenaminones. Conversely from trimethylchlorosilane, the reaction between dianions of 3-(N-isopropylamino)-1-arylbut-2-en-1-ones and t-butyldimethylchlorosilane or triisopropylchlorosilane leads to the corresponding 4-trialkylsilyl derivatives. An explanation of these findings is reported. Hydrolysis of these compounds affords the until now unknown α′ silylated β-diketones.</abstract>
<abstract type="graphical">α′- and γ-Dianions of β-(monoalkylamino) α, β-unsaturated ketones react with trialkylchlorosilanes leading to α′- and γ-trialkylsilylenaminones. Hydrolysis of these compounds affords the until now unknown α′ silylated β-diketones.gr1 </abstract>
<note>Part 7: see ref. 7</note>
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<identifier type="ISSN">0040-4020</identifier>
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