Reaktionen der organischen Chemie

Krauch, Helmut; Kunz, Werner; Nonnenmacher, Eberhard

doi:10.1002/9783527625116

Cited by 12 publications

(12 citation statements)

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“…The crystal was pseudo-merohedrally twinned. The twin relationship (-1 0 0/0 -1 0/1 0 1) was found via TwinRotMat from the Platon program [19] and the batch scale factor refined to 0.140 (2). The X-ray structure refinement produced data to support the following observations: bond lengths and angles were in good agreement with values retrieved from [20].…”

Section: Resultsmentioning

confidence: 85%

“…The identification of the intermediate compound supported the condensation mechanism proposed in 1969 [2], which states that an alcohol of the form (-CH 2 -CHOH-), defined as an alkine in Ref. [7], could be dehydrated during the reaction process to produce a double bond in the final compound [1,2].…”

Section: Resultsmentioning

confidence: 97%

“…[7], could be dehydrated during the reaction process to produce a double bond in the final compound [1,2]. To obtain 2-styrylpyridine as the unique product in a higher yield, it is sufficient to increase the temperature or to include a catalyst such as acetic anhydride, zinc chloride, hydrogen chloride, iodine, or analogous catalysts.…”

Section: Resultsmentioning

confidence: 99%

“…The Knoevenagel condensation has been defined as the reaction between an aldehyde or ketone with any compound having an active methyl and a methylene group being brought on an organic base, ammonia or their salts [2]. The activation of the methylene group is due to the direct attachment of one group such as a nitro, cyano, or acyl moiety, and, in most cases, two such groups are required to provide sufficient activation [3].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde

et al. 2013

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The 1-phenyl-2-(a-pyridyl)ethanol [or 1-phenyl-2-(2-pyridyl)ethanol] compound was obtained from the Knoevenagel condensation reaction between 2-methylpyridine with benzaldehyde without catalyst or solvent. The compound was characterized by IR, 1 H-NMR, and by single crystal X-ray diffraction. The X-ray structure clearly revealed that the compound crystallizes in a monoclinic system with centrosymmetric space group, P2 1 /c, with Z 0 = 1. The unit cell dimensions are a = 5.2481 (3), b = 8.2862(4), c = 23.8498(14) Å , and b = 96.761(5)°. The crystal structure showed the formation of one intermolecular hydrogen bond O-HÁÁÁN between the oxygen atom of the O-H and the nitrogen atom of the pyridine group of the adjacent molecule. The crystallography data gave evidence that the intermediate compound is a new stable 1-phenyl-2-(2-pyridyl)ethanol intermediate which presents an interesting relationship between stability and hydrogen bonds formation in the structure for obtaining similar compounds that have been proposed in the literature.Also, it is shown that it is just before the dehydration process which yields the trans double bond of the 1-phenyl-2-(2-pyridyl)ethene.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde

et al. 2013

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“…[78]) und spater vergessen wird (vgl. [79]). Sie stammt von dem lettischen Chemiker Paul Kulnin (Fig.…”

Section: ) Dass Auch Kuhn Von Der Strukturalen Darstellungsweise Beunclassified

Struktur und Mechanismus in der organischen Chemie im Spiegel von Helvetica Chimica Acta

Heimgartner¹,

Hansen²

1994

Highlights of Chemistry

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Spectroscopic and Theoretical Investigations of Monocyclic Dioximes and Dimethoximes with Six-, Eight-, and Ten-Membered Rings

Strenge

Rademacher²

1999

Eur. J. Org. Chem.

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The dioximes 4–6 and the dimethoximes 7–9, which contain the functional groups in opposite positions of a six‐, eight‐, or ten‐membered ring, were synthesized. Their conformational properties and transannular interactions were investigated by spectroscopic (PE, 13C NMR) and theoretical (MMX, AM1, ab initio HF, and B3LYP) methods. While the cyclooctane derivatives 5 and 8 have conformations favourable for through‐space interactions of the π(CN) orbitals, in the other compounds no such interactions can be ascertained. Through‐space orbital interactions in the molecules with an eight‐membered ring lead to a splitting of the π(CN) MOs of 0.4 eV.

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Reaktionen der organischen Chemie

Cited by 12 publications

References 0 publications

Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde

Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde

Struktur und Mechanismus in der organischen Chemie im Spiegel von Helvetica Chimica Acta

Spectroscopic and Theoretical Investigations of Monocyclic Dioximes and Dimethoximes with Six-, Eight-, and Ten-Membered Rings

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