A1 Journal article – refereed
1-Oxo-1,3-dithiolanes - synthesis and stereochemistry




List of Authors: Pihlaja K, Sinkkonen J, Stajer G, Koch A, Kleinpeter E
Publisher: WILEY-BLACKWELL
Publication year: 2011
Journal: Magnetic Resonance in Chemistry
Journal name in source: MAGNETIC RESONANCE IN CHEMISTRY
Journal acronym: MAGN RESON CHEM
Number in series: 7
Volume number: 49
Issue number: 7
Number of pages: 7
ISSN: 0749-1581

Abstract
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. Copyright (c) 2011 John Wiley & Sons, Ltd.

Last updated on 2019-20-07 at 01:55