Year: 2025
Type: article
Abstract: The results of alkylation of dicarbonyl compounds with 1,2,3-trihalopropane are presented, which is accompanied by rearrangement of the carbon skeleton and leads to the formation of β-substituted furans.Alkylation of β-dicarbonyl compounds with 1,2dibromoethane at room temperature gives a C,C-cycloalkylation product, which isomerizes at a temperature above 180°C into a C,O-dialkylation product, a dihydrofuran derivative.Alkylation of dimetylacetonedicarboxylate with methyl iodide occurs similarly, the primary Oalkylation product undergoes rearrangement into a C-alkylation product at 180°C.It is also shown that such rearrangements occur with small radicals.The product of O-alkylation of dimethylacetone dicarboxylate with dimethyl acetal of bromoacetic aldehyde is stable at a temperature of 200°C, whereas the product of its hydrolysis isomerizes into a product of Calkylation with further conversion into furan derivatives.
Author: Valeh Ismayilov, Gozal Ibrahimova, Isgandar Mamedov, Rakif Qasimov, Niftali Yusubov
Institution: Baku State University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4410476743