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

  • 1-Oxo-1,3-dithiolane (4) and its cis- and trans-2-methyl (5,6), -4-methyl (7,8) and -5-methyl (9,10) derivatives were prepared by oxidizing the corresponding 1,3-dithiolanes (1-3) with NaIO(4) in water. The oxides were purified and their isomers separated using thin layer chromatography. The structural characterization was carried out with (1)H and (13)C NMR spectroscopy and molecular modelling. The sulfoxides 4-6 and 8-10 attain two S(1) type envelopes (sometimes slightly distorted) the S=O(ax) envelope greatly dominating. Cis-4-methyl-1-oxo-1,3-dithiolane is a special case exhibiting both two closely related S=O(ax) (30 and 27%) as well as S=O(eq) (21 and 22%) forms [S(1) and C(4) envelopes, respectively]. The relative energies of these conformations, the values of (1)H-(1)H coupling constants and (1)H and (13)C chemical shifts were estimated by computational methods and they support well the conclusions based on the experimental data.

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Metadaten
Author:Kalevi Pihlaja, Jari Sinkkonen, Geza Stajer, Andreas Koch, Erich Kleinpeter
DOI:https://doi.org/10.1002/mrc.2764
ISSN:0749-1581 (print)
Parent Title (English):Magnetic resonance in chemistry
Publisher:Wiley-Blackwell
Place of publication:Malden
Document Type:Article
Language:English
Year of first Publication:2011
Year of Completion:2011
Release Date:2017/03/26
Tag:(1)H NMR; (13)C NMR; NMR; computational chemistry; conformational analysis; sulfur heterocycles
Volume:49
Issue:7
Pagenumber:7
First Page:443
Last Page:449
Funder:Academy of Finland; Finnish Cultural Foundation
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert