Publication: A DFT Study on the Barton–Kellogg Reaction – The Molecular Mechanism of the Formation of Thiiranes in the Reaction between Diphenyldiazomethane and Diaryl Thioketones
A DFT Study on the Barton–Kellogg Reaction – The Molecular Mechanism of the Formation of Thiiranes in the Reaction between Diphenyldiazomethane and Diaryl Thioketones
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Mlostoń, G., Jasinski, R., Kula, K., & Heimgartner, H. (2020). A DFT Study on the Barton–Kellogg Reaction – The Molecular Mechanism of the Formation of Thiiranes in the Reaction between Diphenyldiazomethane and Diaryl Thioketones. European Journal of Organic Chemistry, 2020(2), 176–182. https://doi.org/10.1002/ejoc.201901443
Abstract
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The mechanism of the reaction of diphenyldiazomethane with thiobenzophenone and related hetaryl thioketones leading to the corresponding tetrasubstituted thiiranes was studied by means of DFT computational methods at the M06-2X/6-311+G(d) level of theory. The study showed that the initial step of this conversion is a classic one-step (3+2) cycloaddition to give 1,3,4-thiadiazolines in a regioselective manner. These initially formed products undergo a spontaneous extrusion of N2 resulting in the formation of tetraaryl-substituted thioc
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- Mlostoń, Grzegorz
- Jasinski, Radomir
- Kula, Karolina
- Heimgartner, Heinz
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Mlostoń, G., Jasinski, R., Kula, K., & Heimgartner, H. (2020). A DFT Study on the Barton–Kellogg Reaction – The Molecular Mechanism of the Formation of Thiiranes in the Reaction between Diphenyldiazomethane and Diaryl Thioketones. European Journal of Organic Chemistry, 2020(2), 176–182. https://doi.org/10.1002/ejoc.201901443
