β-Ketoester — a Rearranged Product of Epoxidation of α, β-Unsaturated Methyl Ester |
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Authors: | A A Ansari F Ahmad S M Osman |
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Abstract: | Attempted epoxidation of long-chain α,β-unsaturated esters resulted in the formation of the rearranged products of the corresponding epoxyesters. It was observed that reaction of peracids with esters of C16, C18 and C22 trans-2-enoic acids, instead of yielding the expected epoxides, gave the isomerized products characterized as β-ketoesters. The structure of β-ketoester as saturated 3-oxoester was unambiguously established by chemical methods as well as by IR, NMR and Mass spectrometry. The selectivity of this rearrangement provides a useful synthetic pathway for the preparation of β-ketoesters. |
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