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Investigations in the field of the stereochemistry of the metal-catalyzed dehydration of 1,3-diols

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Abstract

A study was made of the transformations of cis- and trans-2-hydroxymethyl-cyclohexanol, 2-(α-hydroxyethyl) cyclohexanol and 2-(α-hydroxybutyl) cyclohexanol on Cu/Al and Pt/C catalysts. The primary-secondary diols are mainly converted to oxo compounds containing the same number of carbon atoms, while with the disecondary diols considerable fragmentation too occurs. Aromatization too takes place on Pt/C. The conversion and the transformation directions are practically independent of the spatial configuration, this gives further evidence in support of the mechanism proposed earlier.

Abstract

Изучены превращения цис- и транс-2-гидрокси-метил-циклогексанола, 2-(α-гидрокси-этил)-циклогексанола и 2-(α-гидрокси-бутил)-циклогексанола, в присутствии катализаторов Cu/Al и Pt/C. Первично-вторичные диолы превращаются в оксосоединения с одинаковым числом углеродных атомов, при превращении ди-вторичных диолов в значительной мере наблюдается и фрагментационный процесс. На катализаторе Pt/C происходит также и ароматизация. Глубина превращений и направления реакций практически не зависят от пространственной структуры. Эти результаты являются новым доказательством предположенного нами ранее механизма превращений.

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References

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Authors and Affiliations

  1. Department of Organic Chemistry, Attila József University, Szeged

    Á. Molnár & M. Bartók

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  1. Á. Molnár
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  2. M. Bartók
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Molnár, Á., Bartók, M. Investigations in the field of the stereochemistry of the metal-catalyzed dehydration of 1,3-diols. React Kinet Catal Lett 3, 421–428 (1975). https://doi.org/10.1007/BF02097987

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  • DOI: https://doi.org/10.1007/BF02097987

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