Publication: Reactions of Sulfanyl Chlorides with Thiocamphor and Thiofenchone: Wagner-Meerwein Rearrangement of an Intermediate Thiocarbonylium Ion
Reactions of Sulfanyl Chlorides with Thiocamphor and Thiofenchone: Wagner-Meerwein Rearrangement of an Intermediate Thiocarbonylium Ion
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Majchrzak, A., Mlostoń, G., Linden, A., & Heimgartner, H. (2004). Reactions of Sulfanyl Chlorides with Thiocamphor and Thiofenchone: Wagner-Meerwein Rearrangement of an Intermediate Thiocarbonylium Ion. Helvetica Chimica Acta, 87, 790–799. https://doi.org/10.1002/hlca.200490077
Abstract
Abstract
Abstract
The reaction of sulfanyl and disulfanyl chlorides with thiocamphor (6) in the presence of Et3N leads to unsymmetrical di- and trisulfanes, respectively (Schemes 2 and 4). A reaction mechanism via a thiocarbonylium ion, which is immediately deprotonated, is proposed. The formation of a minor product 10 in the absence of a base, resulting from a Wagner-Meerwein rearrangement, is an additional evidence for the intermediacy of a thiocarbonylium ion (Scheme 3). On the other hand, the non-enolizable thiofenchone (13) reacts with sulfanyl ch
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- Majchrzak, Agnieszka
- Mlostoń, Grzegorz
- Heimgartner, Heinz
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Citations
Majchrzak, A., Mlostoń, G., Linden, A., & Heimgartner, H. (2004). Reactions of Sulfanyl Chlorides with Thiocamphor and Thiofenchone: Wagner-Meerwein Rearrangement of an Intermediate Thiocarbonylium Ion. Helvetica Chimica Acta, 87, 790–799. https://doi.org/10.1002/hlca.200490077
