Beilstein J. Org. Chem.2023,19, 892–900, doi:10.3762/bjoc.19.67
bulkier. The obtained nitrocyclopropane was transformed into furan upon treatment with tin(II) chloride via a ring-opening/ring-closure process.
Keywords: acetoxyiodine; conjugate addition; dihydrofuran; nitroalkene; nitrocyclopropane; Introduction
3-Arylated 2-nitrocyclopropane-1,1-dicarbonylic acid
substituent may prevent the attack of other reagents and suppress the decomposition of the nitrocyclopropane framework.
The chemical transformation of cyclopropane 1e was investigated. When a solution of 1e and tin(II) chloride in benzene was heated at 100 °C for 14 h, successive ring-opening/ring-closure
addition of the 1,3-dicarbonyl compound 3 to nitrostyrene 2 and the α-iodination of the adduct 4, two cyclization modes became possible owing to the ambident property of enol 12. Dihydrofuran 8 was formed in the case of an O-attack, and nitrocyclopropane 1 was formed in the case of a C-attack. Furthermore
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Graphical Abstract
Scheme 1:
Versatile reactivities of cyclopropanes 1a.