Publication: Stereochemical course of the reaction between thiocarbonyl compounds and oxiranes: reaction with cis- and trans-2,3-dimethyloxirane
Stereochemical course of the reaction between thiocarbonyl compounds and oxiranes: reaction with cis- and trans-2,3-dimethyloxirane
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Blagoev, M., Linden, A., & Heimgartner, H. (2000). Stereochemical course of the reaction between thiocarbonyl compounds and oxiranes: reaction with cis- and trans-2,3-dimethyloxirane. Helvetica Chimica Acta, 83, 3163–3178. https://doi.org/10.1002/1522-2675(20001220)83:12<3163::AID-HLCA3163>3.0.CO;2-P
Abstract
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Abstract
The reactions of thiocarbonyl compounds with cis-2,3-dimethyloxirane (1a) in CH2Cl2 in the presence of BF3.Et2O or SnCl4 led to trans-4,5-dimethyl-1,3-oxathiolanes, whereas with trans-2,3-dimethyloxirane (1b) cis-4,5-dimethyl-1,3-oxathiolanes were formed. With the stronger Lewis acid SnCl4 , the formation of side-products was also observed. In the case of 1,3-thiazole-5(4H)-thione 2, these side-products are the corresponding 1,3- thiazol-5(4H)-one 5 and the 1:2 adduct 8 (Schemes 2-4). Their formation can be rationalized by the decompo
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- Blagoev, Milen
- Heimgartner, Heinz
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F. Hoffmann-La Roche AG, Basel
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Blagoev, M., Linden, A., & Heimgartner, H. (2000). Stereochemical course of the reaction between thiocarbonyl compounds and oxiranes: reaction with cis- and trans-2,3-dimethyloxirane. Helvetica Chimica Acta, 83, 3163–3178. https://doi.org/10.1002/1522-2675(20001220)83:12<3163::AID-HLCA3163>3.0.CO;2-P
