Synthesis and some chemical conversions of epoxy alcohols of the cyclohexanone
Authors
M.I. Shatirova
Institute of Polymer Materials of the Ministry of Science and Education of the Republic of Azerbaijan
N.Kh. Gusiyev
Institute of Polymer Materials of the Ministry of Science and Education of the Republic of Azerbaijan
Keywords:
α,β-unsaturated epoxy ketone, β-diketone, Michael reaction, functionally substituted ketoepoxide, intramolecular aldol condensation, epoxy alcohol of the cyclohexanone series
Abstract
The unsaturated epoxyketones of the aliphatic and alicyclic series – 2-methyl-1,2-epoxy-4-hexene-3-one and 2-methyl-5-(cyclohex-3-enyl)-1,2-epoxy-4-hexene-3-one in the presence of sodium ethylate easily undergo the addition reaction with β-diketone – acetylacetone, acetoacetic and malonic esters with formation of primary Michael adducts – functionally substituted ketoepoxides. Their further conversions by intramolecular aldol condensation lead to the formation of epoxy alcohols of the cyclohexanone series. The hydrobromination, bromination and amination of cyclohexanone epoxy alcohols proceeds with the participation of an oxirane and cyclohexene ring, which leads to the formation of new bromo- and amino derivatives of cyclohexanones.
