The formation and reactions of (η5-carboxycyclopentadienyl)dicarbonylcobalt
Identifieur interne : 002023 ( Istex/Corpus ); précédent : 002022; suivant : 002024The formation and reactions of (η5-carboxycyclopentadienyl)dicarbonylcobalt
Auteurs : William P. Hart ; Dong Shihua ; Marvin D. RauschSource :
- Journal of Organometallic Chemistry [ 0022-328X ] ; 1985.
English descriptors
- KwdEn :
- Alumina, Alumina column, Aluminum chloride, Analytical sample, Anhydrous magnesium sulfate, Broad singlet, Calcd, Carbomethoxycyclopentadiene dimer, Carbonate, Carbonyl, Chem, Chloride, Cyclopentadienide, Cyclopentadienyl ring, Deoxygenated, Deoxygenated water, Derivative, Dicobalt octacarbonyl, Diethyl, Diethyl carbonate, Diethyl ether, Dimethyl carbonate, Ether, Green solution, Hydroxide, Iodine crystals, Mercury overpressure valve, Methylene chloride, Mmol, Organic carbonyl band, Oxalyl chloride, Parent compound, Pentane, Pink solution, Potassium hydroxide, Pseudo triplets, Reaction mixture, Room temperature, Sodium carbethoxycyclopentadienide, Sodium carbomethoxycyclopentadienide, Sodium cyclopentadienide, Torr, Viii.
- Teeft :
- Alumina, Alumina column, Aluminum chloride, Analytical sample, Anhydrous magnesium sulfate, Broad singlet, Calcd, Carbomethoxycyclopentadiene dimer, Carbonate, Carbonyl, Chem, Chloride, Cyclopentadienide, Cyclopentadienyl ring, Deoxygenated, Deoxygenated water, Derivative, Dicobalt octacarbonyl, Diethyl, Diethyl carbonate, Diethyl ether, Dimethyl carbonate, Ether, Green solution, Hydroxide, Iodine crystals, Mercury overpressure valve, Methylene chloride, Mmol, Organic carbonyl band, Oxalyl chloride, Parent compound, Pentane, Pink solution, Potassium hydroxide, Pseudo triplets, Reaction mixture, Room temperature, Sodium carbethoxycyclopentadienide, Sodium carbomethoxycyclopentadienide, Sodium cyclopentadienide, Torr, Viii.
Abstract
Abstract: A reaction between sodium cyclopentadienide and dimethyl carbonate in THF solution produces sodium carbomethoxycyclopentadienide in high yield. The analogous carbethoxy derivative can also be readily prepared starting with diethyl carbonate. Carbomethoxycyclopentadienylthallium has been prepared by cracking carbomethoxycyclopentadiene dimer and passing the unstable monomer into an aqueous mixture of thallium(I) chloride and potassium hydroxide. Reactions of these reagents with mixtures of dicobalt octacarbonyl and iodine in THF solution afford moderate yields of the respective products (η5-carbomethoxycyclopentadienyl)dicarbonylcobalt and (η5-carbethoxycyclopentadienyl)dicarbonylcobalt. (η5-Carboxycyclopentadienyl)dicarbonylcobalt is obtained in 67–74% yield by treatment of either ester with potassium hydroxide in aqueous ethanol followed by acidification. A reaction between this acid and oxalyl chloride in benzene solution produces (η5-chloroformylcyclopentadienyl)dicarbonylcobalt in 67% yield, and the latter reacts readily with ammonia and with aniline to form the respective amide and anilide derivatives. The acid chloride also reacts with ferrocene and aluminum chloride under Friedel-Crafts conditions to afford the bimetallic product (η5-ferrocenoylcyclopentadienyl)dicarbonylcobalt. The IR and 1H NMR spectra of these new functionally-substituted derivatives of (η5-cyclopentadienyl)dicarbonylcobalt are discussed.
Url:
DOI: 10.1016/0022-328X(85)87147-3
Links to Exploration step
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<front><div type="abstract" xml:lang="en">Abstract: A reaction between sodium cyclopentadienide and dimethyl carbonate in THF solution produces sodium carbomethoxycyclopentadienide in high yield. The analogous carbethoxy derivative can also be readily prepared starting with diethyl carbonate. Carbomethoxycyclopentadienylthallium has been prepared by cracking carbomethoxycyclopentadiene dimer and passing the unstable monomer into an aqueous mixture of thallium(I) chloride and potassium hydroxide. Reactions of these reagents with mixtures of dicobalt octacarbonyl and iodine in THF solution afford moderate yields of the respective products (η5-carbomethoxycyclopentadienyl)dicarbonylcobalt and (η5-carbethoxycyclopentadienyl)dicarbonylcobalt. (η5-Carboxycyclopentadienyl)dicarbonylcobalt is obtained in 67–74% yield by treatment of either ester with potassium hydroxide in aqueous ethanol followed by acidification. A reaction between this acid and oxalyl chloride in benzene solution produces (η5-chloroformylcyclopentadienyl)dicarbonylcobalt in 67% yield, and the latter reacts readily with ammonia and with aniline to form the respective amide and anilide derivatives. The acid chloride also reacts with ferrocene and aluminum chloride under Friedel-Crafts conditions to afford the bimetallic product (η5-ferrocenoylcyclopentadienyl)dicarbonylcobalt. The IR and 1H NMR spectra of these new functionally-substituted derivatives of (η5-cyclopentadienyl)dicarbonylcobalt are discussed.</div>
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<abstract>A reaction between sodium cyclopentadienide and dimethyl carbonate in THF solution produces sodium carbomethoxycyclopentadienide in high yield. The analogous carbethoxy derivative can also be readily prepared starting with diethyl carbonate. Carbomethoxycyclopentadienylthallium has been prepared by cracking carbomethoxycyclopentadiene dimer and passing the unstable monomer into an aqueous mixture of thallium(I) chloride and potassium hydroxide. Reactions of these reagents with mixtures of dicobalt octacarbonyl and iodine in THF solution afford moderate yields of the respective products (η5-carbomethoxycyclopentadienyl)dicarbonylcobalt and (η5-carbethoxycyclopentadienyl)dicarbonylcobalt. (η5-Carboxycyclopentadienyl)dicarbonylcobalt is obtained in 67–74% yield by treatment of either ester with potassium hydroxide in aqueous ethanol followed by acidification. A reaction between this acid and oxalyl chloride in benzene solution produces (η5-chloroformylcyclopentadienyl)dicarbonylcobalt in 67% yield, and the latter reacts readily with ammonia and with aniline to form the respective amide and anilide derivatives. The acid chloride also reacts with ferrocene and aluminum chloride under Friedel-Crafts conditions to afford the bimetallic product (η5-ferrocenoylcyclopentadienyl)dicarbonylcobalt. The IR and 1H NMR spectra of these new functionally-substituted derivatives of (η5-cyclopentadienyl)dicarbonylcobalt are discussed.</abstract>
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<abstract xml:lang="en"><p>A reaction between sodium cyclopentadienide and dimethyl carbonate in THF solution produces sodium carbomethoxycyclopentadienide in high yield. The analogous carbethoxy derivative can also be readily prepared starting with diethyl carbonate. Carbomethoxycyclopentadienylthallium has been prepared by cracking carbomethoxycyclopentadiene dimer and passing the unstable monomer into an aqueous mixture of thallium(I) chloride and potassium hydroxide. Reactions of these reagents with mixtures of dicobalt octacarbonyl and iodine in THF solution afford moderate yields of the respective products (η5-carbomethoxycyclopentadienyl)dicarbonylcobalt and (η5-carbethoxycyclopentadienyl)dicarbonylcobalt. (η5-Carboxycyclopentadienyl)dicarbonylcobalt is obtained in 67–74% yield by treatment of either ester with potassium hydroxide in aqueous ethanol followed by acidification. A reaction between this acid and oxalyl chloride in benzene solution produces (η5-chloroformylcyclopentadienyl)dicarbonylcobalt in 67% yield, and the latter reacts readily with ammonia and with aniline to form the respective amide and anilide derivatives. The acid chloride also reacts with ferrocene and aluminum chloride under Friedel-Crafts conditions to afford the bimetallic product (η5-ferrocenoylcyclopentadienyl)dicarbonylcobalt. The IR and 1H NMR spectra of these new functionally-substituted derivatives of (η5-cyclopentadienyl)dicarbonylcobalt are discussed.</p>
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<head><ce:title>The formation and reactions of (η<ce:sup>5</ce:sup>
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<ce:author><ce:given-name>Dong</ce:given-name>
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<ce:abstract><ce:section-title>Abstract</ce:section-title>
<ce:abstract-sec><ce:simple-para>A reaction between sodium cyclopentadienide and dimethyl carbonate in THF solution produces sodium carbomethoxycyclopentadienide in high yield. The analogous carbethoxy derivative can also be readily prepared starting with diethyl carbonate. Carbomethoxycyclopentadienylthallium has been prepared by cracking carbomethoxycyclopentadiene dimer and passing the unstable monomer into an aqueous mixture of thallium(I) chloride and potassium hydroxide. Reactions of these reagents with mixtures of dicobalt octacarbonyl and iodine in THF solution afford moderate yields of the respective products (η<ce:sup>5</ce:sup>
-carbomethoxycyclopentadienyl)dicarbonylcobalt and (η<ce:sup>5</ce:sup>
-carbethoxycyclopentadienyl)dicarbonylcobalt. (η<ce:sup>5</ce:sup>
-Carboxycyclopentadienyl)dicarbonylcobalt is obtained in 67–74% yield by treatment of either ester with potassium hydroxide in aqueous ethanol followed by acidification. A reaction between this acid and oxalyl chloride in benzene solution produces (η<ce:sup>5</ce:sup>
-chloroformylcyclopentadienyl)dicarbonylcobalt in 67% yield, and the latter reacts readily with ammonia and with aniline to form the respective amide and anilide derivatives. The acid chloride also reacts with ferrocene and aluminum chloride under Friedel-Crafts conditions to afford the bimetallic product (η<ce:sup>5</ce:sup>
-ferrocenoylcyclopentadienyl)dicarbonylcobalt. The IR and <ce:sup loc="pre">1</ce:sup>
H NMR spectra of these new functionally-substituted derivatives of (η<ce:sup>5</ce:sup>
-cyclopentadienyl)dicarbonylcobalt are discussed.</ce:simple-para>
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<mods version="3.6"><titleInfo><title>The formation and reactions of (η5-carboxycyclopentadienyl)dicarbonylcobalt</title>
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<titleInfo type="alternative" contentType="CDATA"><title>The formation and reactions of (η</title>
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<name type="personal"><namePart type="given">William P.</namePart>
<namePart type="family">Hart</namePart>
<affiliation>Department of Chemistry, University of Massachusetts, Amherst, MA 01003 U.S.A.</affiliation>
<role><roleTerm type="text">author</roleTerm>
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</name>
<name type="personal"><namePart type="given">Dong</namePart>
<namePart type="family">Shihua</namePart>
<affiliation>Department of Chemistry, University of Massachusetts, Amherst, MA 01003 U.S.A.</affiliation>
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<name type="personal"><namePart type="given">Marvin D.</namePart>
<namePart type="family">Rausch</namePart>
<affiliation>Department of Chemistry, University of Massachusetts, Amherst, MA 01003 U.S.A.</affiliation>
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<dateIssued encoding="w3cdtf">1985</dateIssued>
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<language><languageTerm type="code" authority="iso639-2b">eng</languageTerm>
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<abstract lang="en">Abstract: A reaction between sodium cyclopentadienide and dimethyl carbonate in THF solution produces sodium carbomethoxycyclopentadienide in high yield. The analogous carbethoxy derivative can also be readily prepared starting with diethyl carbonate. Carbomethoxycyclopentadienylthallium has been prepared by cracking carbomethoxycyclopentadiene dimer and passing the unstable monomer into an aqueous mixture of thallium(I) chloride and potassium hydroxide. Reactions of these reagents with mixtures of dicobalt octacarbonyl and iodine in THF solution afford moderate yields of the respective products (η5-carbomethoxycyclopentadienyl)dicarbonylcobalt and (η5-carbethoxycyclopentadienyl)dicarbonylcobalt. (η5-Carboxycyclopentadienyl)dicarbonylcobalt is obtained in 67–74% yield by treatment of either ester with potassium hydroxide in aqueous ethanol followed by acidification. A reaction between this acid and oxalyl chloride in benzene solution produces (η5-chloroformylcyclopentadienyl)dicarbonylcobalt in 67% yield, and the latter reacts readily with ammonia and with aniline to form the respective amide and anilide derivatives. The acid chloride also reacts with ferrocene and aluminum chloride under Friedel-Crafts conditions to afford the bimetallic product (η5-ferrocenoylcyclopentadienyl)dicarbonylcobalt. The IR and 1H NMR spectra of these new functionally-substituted derivatives of (η5-cyclopentadienyl)dicarbonylcobalt are discussed.</abstract>
<relatedItem type="host"><titleInfo><title>Journal of Organometallic Chemistry</title>
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<titleInfo type="abbreviated"><title>JOM</title>
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<genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre>
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<dateIssued encoding="w3cdtf">19850226</dateIssued>
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<identifier type="ISSN">0022-328X</identifier>
<identifier type="PII">S0022-328X(00)X1094-7</identifier>
<part><date>19850226</date>
<detail type="volume"><number>282</number>
<caption>vol.</caption>
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<detail type="issue"><number>1</number>
<caption>no.</caption>
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<extent unit="issue-pages"><start>C1</start>
<end>C30</end>
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<end>148</end>
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<identifier type="DOI">10.1016/0022-328X(85)87147-3</identifier>
<identifier type="PII">0022-328X(85)87147-3</identifier>
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