The Production of 4-cis Isomers in the Irradiation of 3-Methyl-5-aryl-2,4-pentadienoic Acids

Wiley, Richard H.; Plas, H. C. van der; Bray, N. F.

doi:10.1021/jo01053a016

J. Org. Chem.

1962

DOI: 10.1021/jo01053a016

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The Production of 4-cis Isomers in the Irradiation of 3-Methyl-5-aryl-2,4-pentadienoic Acids

Richard H. Wiley¹,

H. C. van der Plas²,

N. F. Bray³

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“…As previously noted (1-3), the NMR data provide unequivocal bases for cis-trans structural assignments and evidence of stereochemical purity. The preparational procedures used were similar to those previously described (1)(2)(3).…”

mentioning

confidence: 99%

Cis-Trans Isomers of Methyl Substituted Fluorocinnamic and 5-(o-, m-, and p-Fluorophenyl)-pentadienoic Acids.

Wiley¹,

Plas²

1965

J. Chem. Eng. Data

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mentioning

confidence: 99%

Cis-Trans Isomers of Methyl Substituted Fluorocinnamic and 5-(o-, m-, and p-Fluorophenyl)-pentadienoic Acids.

Wiley¹,

Plas²

1965

J. Chem. Eng. Data

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Kondensation der Äthylester von Croton‐, 3‐Methylcroton‐ und Isopropylidenmalonsäure mit aromatischen Aldehyden

Anghelova

Ivanov

1973

Chem. Ber.

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Unter dcr Einwirkung von Natriumamid in Dimethylformamid entstehen aus den Athylcstern der Croton-und 3-Methylcrotonsiiiure und arornatischen Aldehyden direkt 5-Arylbzw. 5-Aryl-3-methyl-2,4-pcntadiens~uren (3). Unter denselben Bcdingungen iiihrt die Umsctzung der aromatischen Aldehyde mit Isopropylidennialonsaure-diiithylester zu 6-Aryl-4-(2-arylvinyl)-2-oxo-5,6-dihydro-~H-pyran-~-carbonsat~ren (6). Condensation of Ethyl Crotonate, 3-Methylcrotonate, and Isopropylidenemalonate with Aromatic AldehydesWith sodium amide in dimethylformamide ethyl crotonate and 3-methylcrotonate react with aromatic aldehydes to yield directly 5-aryl-and 5-aryl-3-rnethyl-2,4-pentadieiioic acid (3), respectively. Under the same conditions the reaction of aromatic aldehydes with diethyl isopropylidenemalonate leads to h-aryl-4-(2-arylvinyl)-2-oxo-5,6-dihydro-2H-pyran-3-carboxylic acids (6).

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Heterocyclen durch Diensynthese, IV¹⁾ 3‐Hydroxypyrrole aus Diels‐Alder‐Addukten von Nitrosoverbindungen

Kresze

Härtner

1973

Justus Liebigs Ann. Chem.

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Eingegangen am 24. Oktober 19722-Acetoxy-4-aryl-l,3-butadien-l-carbonsaure-methylester 1 werden synthetisiert und mit Nitrosobenzolen 2 zu Gemischen der isomeren Diels-Alder-Addukte 3 und 4 umgesetzt. Die Abhangigkeit des Isomerenverhaltnis 3 : 4 von den Arylsubstituenten in 1 und 2 ist aus dem Mechanismus der Cycloaddition verstandlich. -Die Addukte 3 lassen sich durch Chromatographie an Kieselgel in 3-Hydroxypyrrol-2-carbonsaurederivate 5 iiberfiihren. Heterocycles by Diene Synthesis, CVI). -3-Hydroxypyrroles from Diels-Alder Adducts of Nitroso CompoundsThe methyl 2-acetoxy-4-aryl-l,3-butadiene-l -carboxylates 1 are synthesized and then allowed to react with nitrosobenzenes 2 to give mixtures of the Diels-Alder adducts 3 and 4. The isomer ratio 3 : 4 is dependent on the nature of the aryl substituents in 1 and 2; this dependence may be explained by the mechanism of the cycloaddition. -The adducts 3 are converted into 3-hydroxypyrrole-2-carboxylic acid derivatives by chromatography on silica.Derivate der 3,6-Dihydro-l,2-oxazin-6-carbonsaure-methylester, die bei der DielsAlder-Reaktion von Nitrosoverbindungen rnit Diencarbonsaureestern entstehen, lassen sich in guter Ausbeute durch Behandlung mit Base oder Chromatographie an Aluminiumoxid in Pyrrol-2-carbonsaureester iiberfiihrenl), bei den entsprechenden Addukten aus Dienketonen erfolgt diese Reaktion spontan 2 ) .Um die Anwendungsbreite dieser Pyrrolsynthese zu priifen, haben wir die Diensynthese von 2-Acetoxy-l,3-butadien-l-carbonsaure-methylestern 1 mit Nitrosobenzolen 2 sowie die Moglichkeit zur Umwandlung der dabei gewonnenen Addukte 3 in 3-Hydroxypyrrol-2-carbonsaureester 5 untersucht.

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The Production of 4-cis Isomers in the Irradiation of 3-Methyl-5-aryl-2,4-pentadienoic Acids

Cited by 5 publications

References 0 publications

Cis-Trans Isomers of Methyl Substituted Fluorocinnamic and 5-(o-, m-, and p-Fluorophenyl)-pentadienoic Acids.

Cis-Trans Isomers of Methyl Substituted Fluorocinnamic and 5-(o-, m-, and p-Fluorophenyl)-pentadienoic Acids.

Kondensation der Äthylester von Croton‐, 3‐Methylcroton‐ und Isopropylidenmalonsäure mit aromatischen Aldehyden

Heterocyclen durch Diensynthese, IV¹⁾ 3‐Hydroxypyrrole aus Diels‐Alder‐Addukten von Nitrosoverbindungen

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The Production of 4-cis Isomers in the Irradiation of 3-Methyl-5-aryl-2,4-pentadienoic Acids

Cited by 5 publications

References 0 publications

Cis-Trans Isomers of Methyl Substituted Fluorocinnamic and 5-(o-, m-, and p-Fluorophenyl)-pentadienoic Acids.

Cis-Trans Isomers of Methyl Substituted Fluorocinnamic and 5-(o-, m-, and p-Fluorophenyl)-pentadienoic Acids.

Kondensation der Äthylester von Croton‐, 3‐Methylcroton‐ und Isopropylidenmalonsäure mit aromatischen Aldehyden

Heterocyclen durch Diensynthese, IV1) 3‐Hydroxypyrrole aus Diels‐Alder‐Addukten von Nitrosoverbindungen

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Heterocyclen durch Diensynthese, IV¹⁾ 3‐Hydroxypyrrole aus Diels‐Alder‐Addukten von Nitrosoverbindungen