Abstract:
The reaction of chloral or dichloro(phenyl)acetaldehyde N-arylsulfonylimines with cyclopentadiene, depending on the reaction conditions, affords either Diels–Alder adducts, 2-arylsulfonyl-2-azabicyclo[2.2.1]hept-5-enes, or unexpectedly new amidoalkylated derivatives of cyclopentadiene, N-[(cyclopentadienyl)(polychloromethyl)methyl]arenesulfonamides.
Citation:
G. N. Chernysheva, M. D. Katerinich, I. A. Ushakov, I. B. Rozentsveig, “Diels–Alder trapping vs. amidoalkylation of cyclopentadiene with polychloroacetaldehyde sulfonylimines”, Mendeleev Commun., 30:5 (2020), 618–620
Linking options:
https://www.mathnet.ru/eng/mendc1271
https://www.mathnet.ru/eng/mendc/v30/i5/p618
This publication is cited in the following 4 articles:
Yu. A. Aizina, D. O. Tkachuk, N. S. Shaglaeva, “Synthesis and properties of N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide”, Izvestiâ vuzov. Prikladnaâ himiâ i biotehnologiâ, 14:2 (2024), 150
Gulnur N. Chernysheva, Maxim D. Katerinich, Igor A. Ushakov, Tatiana N. Borodina, Vladimir I. Smirnov, Igor B. Rozentsveig, “Polyhalogenated 2‐Azabicyclo[2.2.1]heptanes from Polyhaloaldimines and Cyclopentadiene via Cycloaddition and Wagner‐Meerwein Rearrangement”, Asian J Org Chem, 13:7 (2024)
E. K Ilyushkina, Ya. V. Veremeychik, O. A Lodochnikova, V. V Plemenkov, “Reactivity of olefin functions of dicyclopentadiene in the Diels-Alder reaction with thionylaniline”, Žurnal obŝej himii, 93:5 (2023), 659
E. K. Ilyushkina, Ya. V. Veremeychik, O. A. Lodochnikova, V. V. Plemenkov, “Reactivity of Olefin Functionalities of Dicyclopentadiene in the Diels–Alder Reaction with Thionylaniline”, Russ J Gen Chem, 93:5 (2023), 1019
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