ALKYLATION REACTIONS OF β-DICARBONYLCOMPOUNDS ACCOMPANIED WITHREARRANGEMENTS

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 -substituted furans.Alkylation of -dicarbonyl compounds with 1,2dibromoethane at room temperature gives a C,C-cycloalkylation product, which isomerizes at a temperature above 180C 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 180C.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 200C, whereas the product of its hydrolysis isomerizes into a product of Calkylation with further conversion into furan derivatives.