First synthesis of acylated nitrocyclopropanes

Abstract
Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination occurs at the α-position of the nitro group, and the subsequent O-attack of the enol moiety leads to 2,3-dihydrofuran. Cyclopropane was successfully synthesized through C-attack as the acyl group became bulkier. The obtained nitrocyclopropane was transformed into furan upon treatment with tin(II) chloride via a ring-opening/ring-closure process.

Beilstein J. Org. Chem. 2023, 19, 892–900. doi:10.3762/bjoc.19.67

Source: Beilstein Journal of Organic Chemistry - June 21, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: acetoxyiodine conjugate addition dihydrofuran nitroalkene nitrocyclopropane Full Research Paper Source Type: research