Tetrahedron

Synthesis of cyclic and acyclic βγ-unsaturated car☐ ylic acids Via an E1-type ionization/elimination of β-lactones

TH Black, SA Eisenbeis, TS McDermott, SL Maluleka

Index: Black, T. Howard; Eisenbeis, Shane A.; McDermott, Todd S.; Maluleka, Stephen L. Tetrahedron, 1990 , vol. 46, p. 2307 - 2316

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Citation Number: 21

Abstract

Cyclic and acyclic ketones were converted in three steps into 3-alkenoic acids, bearing a variety of substituents in the α-position. The sequence, involving ionization/elimination of a β- lactone, affords high yields of pure products uncontaminated with conjugated isomers. Support for an El-type mechanism is also provided.