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β-Ketoester — a Rearranged Product of Epoxidation of α, β-Unsaturated Methyl Ester

✍ Scribed by Ansari, A. A. ;Ahmad, F. ;Osman, S. M.

Publisher: John Wiley and Sons
Year: 1977
Weight: 345 KB
Volume: 79
Category: Article
ISSN: 0931-5985
DOI: 10.1002/lipi.19770790807

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✦ Synopsis

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 C~16~, C~18~ and C~22~ 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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