Publication: Selenophen-2-yl-substituted thiocarbonyl ylides – at the borderline of dipolar and biradical reactivity
Selenophen-2-yl-substituted thiocarbonyl ylides – at the borderline of dipolar and biradical reactivity
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Mlostoń, G., Urbaniak, K., Linden, A., & Heimgartner, H. (2015). Selenophen-2-yl-substituted thiocarbonyl ylides – at the borderline of dipolar and biradical reactivity. Helvetica Chimica Acta, 98(4), 453–461. https://doi.org/10.1002/hlca.201500050
Abstract
Abstract
Abstract
The reactions of aryl (selenophen-2-yl) thioketones with CH2N2 occur with spontaneous elimination of N2, even at low temperature (-65°), to give regioselectively sterically crowded 4,4,5,5-tetrasubstituted 1,3-dithiolanes and/or a novel type of twelve-membered dithia-diselena heterocycles as dimers of the transient thiocarbonyl S-methanides. The ratio of these products depends on the type of substituent located at C(4) of the phenyl ring. Whereas the formation of the 1,3-dithiolanes corresponds to a [3 + 2] cycloaddition of an interme
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- Mlostoń, Grzegorz
- Urbaniak, Katarzyna
- Heimgartner, Heinz
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Citations
Mlostoń, G., Urbaniak, K., Linden, A., & Heimgartner, H. (2015). Selenophen-2-yl-substituted thiocarbonyl ylides – at the borderline of dipolar and biradical reactivity. Helvetica Chimica Acta, 98(4), 453–461. https://doi.org/10.1002/hlca.201500050
