Ketenimine: geometrie und abhängigkeit der razemisierungsbarriere von den substituenten

Jochims, Johannes C.; Herzberger, Siegfried; Gambke, Brigitte; Anet, Frank A. L.

doi:10.1016/s0040-4039(01)83734-5

Tetrahedron Letters

1977

DOI: 10.1016/s0040-4039(01)83734-5

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Ketenimine: geometrie und abhängigkeit der razemisierungsbarriere von den substituenten

Johannes C. Jochims

Siegfried Herzberger

Brigitte Gambke

et al.

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Cited by 15 publications

(6 citation statements)

References 10 publications

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“…catalysis to rate-determining protonation on carbon From the data in Table2it is clear that the dimethylketenimine(11) reacts ca. 100-fold more rapidly with H,O+ than does the C-phenyl analogue (9e).…”

mentioning

confidence: 99%

Rapid acid-catalysed and uncatalysed hydration of ketenimines

McCarthy¹,

Hegarty²

1980

J. Chem. Soc., Perkin Trans. 2

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mentioning

confidence: 99%

Rapid acid-catalysed and uncatalysed hydration of ketenimines

McCarthy¹,

Hegarty²

1980

J. Chem. Soc., Perkin Trans. 2

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“…[6][7][8][9] The spectroscopic properties of ketenimines have been intensively investigated. 10,11 We wish to report a simple one-pot preparation of stable ketenimines using tert-butyl isocyanide, dialkyl acetylenedicarboxylates 1, and a strong NH-acid, such as alkyl arylamino-2-oxo-acetates 2a-2c. This three-component condensation reaction produces highly functionalised ketenimines 3 in fairly good yields (Scheme 1).…”

mentioning

confidence: 99%

Synthesis and Dynamic NMR Study of Fluorinated Dialkyl 2-[(tert-butylimino)-methylene]-3-[(2-alkoxy-2-oxoacetyl)-2-fluoroanilino]-succinates

Yavari

Nasiri

Djahaniani

et al. 2005

Journal of Chemical Research

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The 1:1 adduct produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped by alkyl 2-fluoro-anilino-2-oxo-acetates or ethyl 2-oxo-2-(trifluoromethylanilino)-acetate to produce functionalised ketenimines in good yields. Dynamic NMR effects were observed in the 1H NMR spectra of these compounds as a result of restricted rotation around the single bond linking the aryl group to the ketenimine system. The free energy of activation (ΔG≠) for this process is 64.9–66.5 kJ mol−1.

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“…[1][2][3][4][5] The spectroscopic properties of ketenimines have been intensively investigated. 6,7 We wish to report a simple one-pot preparation of stable ketenimines using alkyl isocyanides 1, dialkyl acetylenedicarboxylates 2, and a strong CH-acid, such as methyl 2-acetyl-3-oxobutanoate. This condensation reaction produces highly functionalized ketenimines 3 in fairly good yields.…”

mentioning

confidence: 99%

A simple synthesis of highly functionalized ketenimines

Yavari

Nourmohammadian

2000

Journal of Chemical Research

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Compounds containing a heterocumulene entity are expected to have synthetic potential as a result of their ability to take part in dimerization, cycloaddition, and polymerization, among other reactions. 1 In general, hydrogen substituted ketenimines and those with small unbranched alkyl substituents are elusive substances. Ketenimines play a role as discrete but transient intermediates in many interconversions, especially in eliminationaddition processes and in the formation of heterocyclic systems. [1][2][3][4][5] The spectroscopic properties of ketenimines have been intensively investigated. 6,7 We wish to report a simple one-pot preparation of stable ketenimines using alkyl isocyanides 1, dialkyl acetylenedicarboxylates 2, and a strong CH-acid, such as methyl 2-acetyl-3-oxobutanoate. This condensation reaction produces highly functionalized ketenimines 3 in fairly good yields. These ketenimines are recovered unchanged after refluxing a chloroform solution for several hours.The structures of compounds 3a-c were deduced from their elemental analyses, mass spectrometric data and their 1 H and 13 C NMR and IR spectra. The nature of these compounds as 1:1:1 adducts was apparent from the mass spectra which displayed molecular ion peaks at m/z = 383, 411, and 409.The 1 H NMR spectra of 3a exhibited seven single sharp lines arising from tert-butyl (δ = 1.40 ppm), acetyl (δ = 2.31 and 2.36 ppm), methoxy (δ = 3.60, 3.62 and 3.80 ppm), and the methine (δ = 4.62 ppm) protons. The 13 C NMR spectrum of 3a showed sixteen distinct resonances consistent with the dimethyl 2-(N-tertbutyliminomethylidene)-3(1-acetyl-1-methoxycarbonyl-2oxopropyl)succinate 3a. Partial assignments of these resonances are given in the experimental section.

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Ketenimine: geometrie und abhängigkeit der razemisierungsbarriere von den substituenten

Cited by 15 publications

References 10 publications

Rapid acid-catalysed and uncatalysed hydration of ketenimines

Rapid acid-catalysed and uncatalysed hydration of ketenimines

Synthesis and Dynamic NMR Study of Fluorinated Dialkyl 2-[(tert-butylimino)-methylene]-3-[(2-alkoxy-2-oxoacetyl)-2-fluoroanilino]-succinates

A simple synthesis of highly functionalized ketenimines

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