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The stereochemistry of some new chiral brominated compounds with a 2,4,8,10-tetraoxaspiro[5.5]undecanic skeleton

Zur Stereochemie einiger neuer chiraler Bromverbindungen mit einem 2,4,8,10-Tetraoxaspiro[5.5]-undecan — Gerüst

  • Organische Chemie Und Biochemie
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Summary

New compounds containing the 2,4,8,10-tetraoxaspiro[5.5]undecanic skeleton, substituted with brominated groups, have been synthesized by a regioselective radicalic bromination reaction. The stereochemistry of the compounds was studied by high resolution NMR methods. The anancomericity or the flipping of the rings was inferred from the conformational analysis. The chirality of the spiranic skeleton was investigated by means of the diastereotopicity of hydrogen and carbon atoms.

Zusammenfassung

Mittels einer regioselektiven radikalischen Bromierungsreaktion wurden neue bromsubstituierte Verbindungen mit einem 2,4,8,10-Tetraoxaspiro[5.5]undecan — Gerüst synthetisiert. Die Stereochemie der Verbindungen wurde mit Hilfe hochauflösender Kernresonanzspektroskopie untersucht. Die Chiralität des Spiranskeletts wird im Zusammenhang mit der Diastereotopie von Wasserstoff- und Kohlenstoffatomen diskutiert.

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Authors and Affiliations

  1. Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Ciudad Universitaria, 041510 D.F., Mexico

    I. Grosu, R. Martinez & R. R. Gaviño

  2. Organic Chemistry Department, Babes-Bolyai University, RO-3400, Cluj-Napoca, Romania

    S. Mager & M. Horn

  3. Laboratoire Associé au CNRS DO-464, Faculté des Sciences de Rouen, Université de Rouen et IRCOF, F-76821, Mont Saint Aignan, France

    G. Plé

Authors
  1. I. Grosu
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  2. S. Mager
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  3. G. Plé
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  4. R. Martinez
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  5. M. Horn
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  6. R. R. Gaviño
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Additional information

On leave from Organic Chemistry Department, Babes-Bolyai University, RO-3400 Cluj-Napoca, Romania

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Grosu, I., Mager, S., Plé, G. et al. The stereochemistry of some new chiral brominated compounds with a 2,4,8,10-tetraoxaspiro[5.5]undecanic skeleton. Monatsh Chem 126, 1021–1030 (1995). https://doi.org/10.1007/BF00811022

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  • DOI: https://doi.org/10.1007/BF00811022

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