Two New Norcaradiene‐Cycloheptatriene Equilibria

Günther, Harald; Tunggal, Budi; Regitz, Manfred; Scherer, Hans; Keller, Toni

doi:10.1002/anie.197105631

Cited by 27 publications

(4 citation statements)

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“… a Calculated Gibbs free energy of the NCD-isomer relative to the CHT-isomer. b Calculated relative Gibbs free energy of the transition states for CHT → NCD. c In kcal/mol, it is the DFT B3LYP-D3/6-311+G(d,p) level with the SMD model for the solvent. d Experimental estimation of the position of equilibria CHT/NCD according to NMR or Raman spectroscopy. e Experimentally estimated, the equilibrium constant K = 0.4 and the calculated equilibrium constant K = 0.3. …”

Section: Results and Discussionmentioning

confidence: 98%

“… e Experimentally estimated, the equilibrium constant K = 0.4 and the calculated equilibrium constant K = 0.3. …”

Section: Results and Discussionmentioning

confidence: 98%

“…d Experimental estimation of the position of equilibria CHT/NCD according to NMR or Raman spectroscopy. e Experimentally estimated, the equilibrium constant K = 0.422 and the calculated equilibrium constant K = 0.3.…”

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confidence: 98%

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Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds

et al. 2021

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The reaction conditions for the Buchner reaction of 2-(diazoacetyl)-2H-azirines with benzene leading to 2-(cyclohepta-2,4,6-trien-1-yl)-2H-azirines have been found. The azirine fragment of these compounds was subsequently used to prepare 5-(cyclohepta-2,4,6-trien-1-yl)isoxazoles and α-(cyclohepta-2,4,6-triene-1-ylcarbonyl)-1H-pyrroles. NMR and DFT calculations showed that the cycloheptatriene-norcaradiene valence isomerization in the corresponding moieties of synthesized azirines, isoxazoles, and pyrroles is very fast at room temperature. Cycloheptatriene valence isomer predominates in azirines and pyrroles, while 5-(cycloheptatrienyl)isoxazoles exist in a pure cycloheptatriene form at 25 °C in chloroform solution. In accordance with the X-ray analysis, two of the synthesized pyrroles crystallized as norcaradiene isomers from a solution of equilibrium mixture of valence isomers. Reductive isoxazole ring opening using the Mo(CO)6/H2O reductive system afforded (Z)-3-amino-3-aryl-1-(cyclohepta-2,4,6-trien-1-yl)prop-2-en-1-ones, which are pure cycloheptatriene isomers. α-(Cycloheptatrieneylcarbonyl)-1H-pyrroles were transformed into the α-(benzylcarbonyl)-1H-pyrroles under cooperative TFA/Rh2(TFA)4 catalysis.

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Section: Results and Discussionmentioning

confidence: 98%

“… e Experimentally estimated, the equilibrium constant K = 0.4 and the calculated equilibrium constant K = 0.3. …”

Section: Results and Discussionmentioning

confidence: 98%

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Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds

et al. 2021

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“…Various spectrometric and spectroscopic studies viz. mass spectrometry [6][7][8], photoelectron [9,10], dipole laser [11], Fourier transform infrared absorption [12], and infrared chemiluminescence [13] spectroscopies have also confirmed its presence in atmosphere and interstellar media. FO acts as an intermediate of F 2 O thermal dissociation [9][10][11] and in the photochemical reaction between F 2 O and SO 3 [14].…”

Section: Introductionmentioning

confidence: 99%

Electron scattering from FO

Modak¹,

Antony²

2019

J. Phys. B: At. Mol. Opt. Phys.

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We report a theoretical investigation of electron scattering from FO radical for incident energies 0.1–15 eV. Calculations were performed for static exchange (SE), SE with polarization and configuration-interaction methods independently to study ground state, polarization effect and excited state contributions precisely. The R-matrix method was used for the present calculations. Results are presented in terms of elastic differential, elastic integral, elastic partial cross section for this radical. All states below the ionization threshold were included to augment the final wave function in the continuum. Two bound states were detected at 1.91 and 3.94 eV for the triplet scattering state. Calculations were also made for dipole allowed transitions, X2Π A2Π, X2Π 2Σ and X2Π 2Δ, below ionization potential. These transitions were considered for excitation cross section study.

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Stereochemical Aspects of¹³C NMR Spectroscopy

Wilson

Stothers

1974

Topics in Stereochemistry

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Two New Norcaradiene‐Cycloheptatriene Equilibria

Abstract: The state with desorption maximum between 200" and 265 "K is the only one occurring at 0 < 0.05. It follows from

Cited by 27 publications

References 4 publications

Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds

Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds

Electron scattering from FO

Stereochemical Aspects of¹³C NMR Spectroscopy

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Two New Norcaradiene‐Cycloheptatriene Equilibria

Abstract: The state with desorption maximum between 200" and 265 "K is the only one occurring at 0 < 0.05. It follows from

Cited by 27 publications

References 4 publications

Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds

Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds

Electron scattering from FO

Stereochemical Aspects of13C NMR Spectroscopy

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Stereochemical Aspects of¹³C NMR Spectroscopy