8(S)-[(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyloxy]-3,4-dihydro-2H-[1,4]dithiepino[2,3-c]furan-6(8H)-one

The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an optically a...

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Bibliographic Details
Published in:MolBank 2024-06, Vol.2024 (2), p.M1820
Main Authors: Khabibrakhmanova, Alsu M., Rabbanieva, Enze S., Gerasimova, Darya P., Latypova, Liliya Z., Kurbangalieva, Almira R.
Format: Article
Language:English
Subjects:
2(5H)-furanone
bis-thioether
Carbon
Cesium
Chromatography
Optical activity
Potassium hydroxides
Propane
propane-1,3-dithiol
S,O-heterocycle
Single crystals
Sulfur
thiolate–thiolate exchange
trans-thiylation
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Summary:The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an optically active fused bicyclic sulfur heterocycle, possessing 1,4-dithiepine and unsaturated γ-lactone moieties. The studied reaction follows an unexpected pathway in a basic medium with the thiolate–thiolate exchange. The structure of the novel heterocycle of the 1,4-dithiepinofuranone series is characterized by single-crystal X-ray diffraction.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1820