Configurational analysis of diastereomeric open‐chain and cyclic nitro‐substituted diols by NMR spectroscopy

P. Sohár, Gy Mikite, I. Pelczer, Kovács, A. Kis‐Tamás

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Abstract

Nitro‐substituted 1,3‐dioxanes and pyrans with potential biological activity were synthesized. The relative configurations of the threo and erythro isomers of 2‐nitro‐1‐phenylpropane‐1,3‐diol (the starting materials) and of 5‐nitro‐2,4‐diphenyl‐1,3‐dioxane, the products formed with benzaldehyde, were determined by 1H and 13C NMR spectroscopy. Cinnamaldehyde and nitroethanol give a homologue of nitrophenylpropanediol, which exists as a mixture of two diastereomeric cyclic hemiacetals. After dissolving in CDCl3, the ratio of these components changes from approximately 10:1 to 3:2 in a few days. The ethyl acetal of the hemiacetal is stereohomogeneous, and the ethoxy group is axial to the pyran ring owing to the anomeric effect. This configuration was proved by two‐dimensional NMR measurement, permitting separate observation of the originally overlapping multiplets and direct reading of the H,H coupling constants.

Original languageEnglish
Pages (from-to)710-716
Number of pages7
JournalOrganic Magnetic Resonance
Volume22
Issue number11
DOIs
Publication statusPublished - 1984

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ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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