X-ray, IR and 1H-NMR structural and conformational study of highly congested 2-alkyl-1,3-diols and of 3-(1-adamantyl)pentane-2,4-dione

M. Moreno-Mañas, J. F. Piniella, A. Alvarez-Larena, N. Galvez, M. E. Lloris, J. Marquet, A. C. Siani, G. Germain

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2 Citations (Scopus)

Abstract

Configuration of meso diols produced by LiA1H4 reduction of symmetric α-(1-adamantyl)-β-diketones has been determined by X-ray diffraction. Large C-C distances and C-C-C angles have been measured for these strained molecules. Most of the studied 1,3-diols, both meso and d,1, exist in solution in conformations possesing intramolecular hydrogen bond. The conformations of two diols were also studied in the crystal phase. © 1992.
Original languageEnglish
Pages (from-to)3611-3622
JournalTetrahedron
Volume48
Issue number17
DOIs
Publication statusPublished - 1 Jan 1992

Keywords

  • Configuration determination
  • conformational analysis
  • hydrogen bond
  • infrared and 1H-NMR spectroscopy
  • pseudoasymmetric atoms
  • X-ray diffraction

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