Diradical reaction mechanisms in [3 + 2]-cycloadditions of hetaryl thioketones with alkyl- or trimethylsilyl-substituted diazomethanes

Scholarly Works

• Amankwah, G.; Ofori, I.; Atta-Kumi, J.; Kwawu, C. R.; Tia, R.; Adei, E. A quantum mechanistic insight into the chemo- and regio-selective [3 + 2]-cycloaddition reaction of aryl hetaryl thioketones with diazoalkanes and nitrile oxide derivatives. Journal of molecular graphics & modelling 2023, 120, 108418. doi:10.1016/j.jmgm.2023.108418
• Song, S.-M.; Jin, J.; Choi, J.-H.; Chung, W.-J. Synthesis of cis-thiiranes as diastereoselective access to epoxide congeners via 4π-electrocyclization of thiocarbonyl ylides. Nature communications 2022, 13, 4818. doi:10.1038/s41467-022-32499-3
• Daraosheh, A. Q.; Abul-Futouh, H.; Murakami, N.; Ziems, K. M.; Görls, H.; Kupfer, S.; Gräfe, S.; Ishii, A.; Celeda, M.; Mlostoń, G.; Weigand, W. Novel [FeFe]-Hydrogenase Mimics: Unexpected Course of the Reaction of Ferrocenyl α-Thienyl Thioketone with Fe3(CO)12. Materials (Basel, Switzerland) 2022, 15, 2867. doi:10.3390/ma15082867
• Lin, X.; Pu, M.; Sang, X.; Li, S.; Liu, X.; Wu, Y.; Feng, X. Asymmetric Catalytic (2+1) Cycloaddition of Thioketones to Synthesize Tetrasubstituted Thiiranes. Angewandte Chemie 2022, 134. doi:10.1002/ange.202201151
• Lin, X.; Pu, M.; Sang, X.; Li, S.; Liu, X.; Wu, Y.-D.; Feng, X. Asymmetric Catalytic (2+1) Cycloaddition of Thioketones to Synthesize Tetrasubstituted Thiiranes. Angewandte Chemie (International ed. in English) 2022, 61, e202201151. doi:10.1002/anie.202201151
• Plażuk, D.; Łomzik, M.; Chrabąszcz, K.; Wieczorek-Błauż, A. Thiiranes and Thiirenes: Monocyclic. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 361–412. doi:10.1016/b978-0-12-409547-2.14786-9
• Mlostoń, G.; Kula, K.; Jasiński, R. A DFT Study on the Molecular Mechanism of Additions of Electrophilic and Nucleophilic Carbenes to Non-Enolizable Cycloaliphatic Thioketones. Molecules (Basel, Switzerland) 2021, 26, 5562. doi:10.3390/molecules26185562
• Mlostoń, G.; Kowalczyk, M.; Augustin, A. U.; Jones, P. G.; Werz, D. B. Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes. European journal of organic chemistry 2021, 2021, 6250–6253. doi:10.1002/ejoc.202100879
• Mlostoń, G.; Urbaniak, K.; Sobiecka, M.; Heimgartner, H.; Würthwein, E.-U.; Zimmer, R.; Lentz, D.; Reissig, H.-U. Hetero-Diels-Alder Reactions of In Situ-Generated Azoalkenes with Thioketones; Experimental and Theoretical Studies. Molecules (Basel, Switzerland) 2021, 26, 2544. doi:10.3390/molecules26092544
• Benhamed, L.; Mekelleche, S. M.; Benchouk, W.; Charif, I. E.; Ríos-Gutiérrez, M.; Domingo, L. R. Understanding the Influence of the Trifluoromethyl Group on the Selectivities of the [3+2] Cycloadditions of Thiocarbonyl S-methanides with α,β-Unsaturated Ketones. A MEDT study. ChemistrySelect 2020, 5, 12791–12806. doi:10.1002/slct.202002923
• Domingo, L. R.; Acharjee, N.; Mohammad-Salim, H. A. Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective. Organics 2020, 1, 3–18. doi:10.3390/org1010002
• Buday, P.; Seeber, P.; Zens, C.; Abul-Futouh, H.; Görls, H.; Gräfe, S.; Matczak, P.; Kupfer, S.; Weigand, W.; Mlostoń, G. Iron(0)-Mediated Stereoselective (3+2)-Cycloaddition of Thiochalcones via a Diradical Intermediate. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 11412–11416. doi:10.1002/chem.202001412
• Mlostoń, G.; Kowalczyk, M.; Augustin, A. U.; Jones, P. G.; Werz, D. B. Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor-acceptor cyclopropanes. Beilstein journal of organic chemistry 2020, 16, 1288–1295. doi:10.3762/bjoc.16.109
• Mlostoń, G.; Jasiński, R.; Kula, K.; Heimgartner, H. 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 2019, 2020, 176–182. doi:10.1002/ejoc.201901443
• Murai, T. The Construction and Application of C=S Bonds. Topics in current chemistry (Cham) 2018, 376, 31. doi:10.1007/s41061-018-0209-0
• Mlostoń, G.; Hamera-Fałdyga, R.; Urbaniak, K.; Weigand, W.; Heimgartner, H. A convenient access to 1,2-diferrocenyl-substituted ethylenes via [3 + 2]-cycloelimination of 2-silylated 4,4,5,5-tetrasubstituted 1,3-dithiolanes. Journal of Sulfur Chemistry 2018, 39, 516–524. doi:10.1080/17415993.2018.1485920
• Mohtat, B.; Siadati, S. A.; Khalilzadeh, M. A.; Zareyee, D. The concern of emergence of multi-station reaction pathways that might make stepwise the mechanism of the 1,3-dipolar cycloadditions of azides and alkynes. Journal of Molecular Structure 2018, 1155, 58–64. doi:10.1016/j.molstruc.2017.10.034
• Mlostoń, G.; Hamera-Fałdyga, R.; Heimgartner, H. Silylated thiocarbonyl S-methanides as key intermediates in one-pot olefination reactions leading to ferrocenyl-substituted ethenes and dibenzofulvenes. Journal of Sulfur Chemistry 2017, 39, 267–278. doi:10.1080/17415993.2017.1415339
• Mlostoń, G.; Pipiak, P.; Hamera-Fałdyga, R.; Heimgartner, H. A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes. Beilstein journal of organic chemistry 2017, 13, 1900–1906. doi:10.3762/bjoc.13.185
• Utecht, G.; Sioma, J.; Jasiński, M.; Mlostoń, G. Expected and unexpected results in reactions of fluorinated nitrile imines with (cyclo)aliphatic thioketones. Journal of Fluorine Chemistry 2017, 201, 68–75. doi:10.1016/j.jfluchem.2017.07.014

Explore citations to this article at