G. N. Chernysheva, M. D. Katerinich, I. A. Ushakov, I. B. Rozentsveig, “Diels–Alder trapping vs. amidoalkylation of cyclopentadiene with polychloroacetaldehyde sulfonylimines”, Mendeleev Commun., 2020, Volume 30, Issue 5,Pages <nobr>618

This article is cited in 4 papers

Communications

Diels–Alder trapping vs. amidoalkylation of cyclopentadiene with polychloroacetaldehyde sulfonylimines

G. N. Chernysheva, M. D. Katerinich, I. A. Ushakov, I. B. Rozentsveig

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

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.

Keywords: sulfonylimines, dienophiles, C-amidoalkylation, Diels–Alder cycloaddition, cyclopentadiene, aldimines, chloral.

Language: English

DOI: 10.1016/j.mencom.2020.09.022

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