Heterocyclische β-enamino-ester-V. Spektroskopische untersuchungen zur struktur heterocyclischer β-enamino-ester

H. Wamhoff, H. W. Dürbeck, P. Sohár

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Abstract

UV, IR, and NMR spectra of 23 β-enamino-esters are described. The bathochromic shift in the UV spectra confirms a considerable π-electron delocalization. From the IR spectra follows, that the 2-standing amino function is not chelated to the neighbouring ester carbonyl. Deuterium exchange experiments show, that the bands of the enamino-carbonyl group must be considered as absorptions of group frequencies EI, EII and EIII, The NMR spectra reveal, that all potential tautomeric compounds described exist predominantly in the enamine form. The amine proton resonance position confirms the unchelated form. From the spectroscopic data certain correlations regarding the stability and chemical properties of these compounds can be drawn.

Original languageEnglish
Pages (from-to)5873-5891
Number of pages19
JournalTetrahedron
Volume27
Issue number23
DOIs
Publication statusPublished - 1971

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Esters
Nuclear magnetic resonance
Deuterium
Chemical properties
Amines
Protons
Electrons
Experiments

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Heterocyclische β-enamino-ester-V. Spektroskopische untersuchungen zur struktur heterocyclischer β-enamino-ester. / Wamhoff, H.; Dürbeck, H. W.; Sohár, P.

In: Tetrahedron, Vol. 27, No. 23, 1971, p. 5873-5891.

Research output: Contribution to journalArticle

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AB - UV, IR, and NMR spectra of 23 β-enamino-esters are described. The bathochromic shift in the UV spectra confirms a considerable π-electron delocalization. From the IR spectra follows, that the 2-standing amino function is not chelated to the neighbouring ester carbonyl. Deuterium exchange experiments show, that the bands of the enamino-carbonyl group must be considered as absorptions of group frequencies EI, EII and EIII, The NMR spectra reveal, that all potential tautomeric compounds described exist predominantly in the enamine form. The amine proton resonance position confirms the unchelated form. From the spectroscopic data certain correlations regarding the stability and chemical properties of these compounds can be drawn.

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