3-Oxo-1,3-oxathiolanes-synthesis and stereochemistry

Kalevi Pihlaja, Jari Sinkkonen, Géza Stájer

Research output: Article

4 Citations (Scopus)

Abstract

The compound 3-oxo-1,3-oxathiolane (6) and its cis- and trans-2-methyl (7,8), 4-methyl (9,10), 5-methyl (11,12) and 2-p-nitrophenyl (13,14) derivatives were prepared by oxidizing the corresponding 1,3-oxathiolanes (1-5) with NalO4 in water. The oxides were purified and their isomers separated using thin layer chromatography. The structural characterization was carried out with 1H NMR spectroscopy and molecular modeling. Compounds 8-10,12, and 14 attain the half-chair type conformation with O(1) above and C(S) below the plane (HC1), but 6, 7, 11, and 13 are, for steric reasons, the mixtures with the alternative half-chair (HC2), where O(1) is below and C(5) above this plane. Accordingly, 6 appears based on the values of experimental coupling constants as an 81:19, 7 as a 37:63, 11 as a 33:67 and 13 as a 54:46 mixture of HC1 and HC2, respectively. The relative energies of these conformations, the values of the vicinal H,H-coupling constants and 1H chemical shifts were estimated for compounds 6-12 also by computational methods and they support nicely the conclusions based on experimental data.

Original languageEnglish
Pages (from-to)244-249
Number of pages6
JournalMagnetic Resonance in Chemistry
Volume46
Issue number3
DOIs
Publication statusPublished - márc. 1 2008

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ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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