A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
1-Oxo-1,3-dithiolanes - synthesis and stereochemistry
Tekijät: Pihlaja K, Sinkkonen J, Stajer G, Koch A, Kleinpeter E
Kustantaja: WILEY-BLACKWELL
Julkaisuvuosi: 2011
Journal: Magnetic Resonance in Chemistry
Tietokannassa oleva lehden nimi: MAGNETIC RESONANCE IN CHEMISTRY
Lehden akronyymi: MAGN RESON CHEM
Numero sarjassa: 7
Vuosikerta: 49
Numero: 7
Aloitussivu: 443
Lopetussivu: 449
Sivujen määrä: 7
ISSN: 0749-1581
DOI: https://doi.org/10.1002/mrc.2764
Tiivistelmä
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.
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.
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