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Stereochemie und1H-NMR-Spektren einiger Spiro-1,3-Dioxane

Stereochemistry and1H-NMR spectra of some spiro-1,3-dioxanes

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Mono and dispiro-1,3-dioxanes (1–3) were synthesized by the condensation of 1,2-, 1,3- and 1,4-cyclohexanedione, respectively (4–6) with bis-(hydroxymethyl)-malonic ester (7). The1H-NMR spectra prove for the mono- (2) and dispiro-1,3-dioxane (3) the existence of conformational equilibria and for the monospiro-1,3-dioxane (1) a “fixed” structure. C6D6 causes a remarkable solvent shift effect in the NMR spectra separating a superposed complex coupling pattern (in CDCl3) in two well resolved AB doublets and two AX quartets. TheE-oxime of the monospiro-1,3-dioxanone (1) represents also a “fixed” structure. Bis-(hydroxymethyl)-malonic ester (7) is a formaldehyde generating agent in the condensation reaction of dimedone with the diol7.

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Literatur

  1. Mager S., Eliel E., Rev. Roum. Chim.18, 1379 (1973).

    Google Scholar 

  2. Mager S., Eliel E., Rev. Roum. Chim.18, 2097 (1973).

    Google Scholar 

  3. Binsch G., Eliel E., Mager S., J. Org. Chem.38, 4079 (1973).

    Google Scholar 

  4. Kaloustian M., Dennis N., Mager S., Evans S., Alcudia F., Eliel E., J. Amer. Chem. Soc.98, 956 (1976).

    Google Scholar 

  5. Mager S., Hopârtean I., Horn M., Grosu I., Stud. Univ. Babeş-Bolyai, Chem.24 (1), 32 (1979).

    Google Scholar 

  6. Jackman L. M., Sternhell S., Applications of NMR-spectroscopy in organic chemistry, S. 53. New York: Pergamon. 1969.

    Google Scholar 

  7. Block P., Org. Synth.40, 27 (1960).

    Google Scholar 

  8. Vogel A. I., Practical organic chemistry, S. 975. London: Longmans, Green. 1956.

    Google Scholar 

  9. Thompson R. B., Org. Synth., Coll.3, 278 (1955).

    Google Scholar 

  10. Nielsen A. T., Carpenter W. R., Org. Synth.45, 25 (1965).

    Google Scholar 

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Authors and Affiliations

  1. Lehrstuhl für organische Chemie und Technologie, Universität „Babeş-Bolyai“, Cluj-Napoca, Rumänien

    Sorin Mager, Ruxandra TĂranu, Mihai Horn & Mariana Mureşan

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  1. Sorin Mager
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  2. Ruxandra TĂranu
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  3. Mihai Horn
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  4. Mariana Mureşan
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Mager, S., TĂranu, R., Horn, M. et al. Stereochemie und1H-NMR-Spektren einiger Spiro-1,3-Dioxane. Monatsh Chem 113, 565–572 (1982). https://doi.org/10.1007/BF00800263

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  • DOI: https://doi.org/10.1007/BF00800263

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