SYNTHETIS OF CYCLIC AND ACYCLIC β,γ-UNSATURATED CARBOXYLIC ACIDS VIA AN E1-TYPE IONIZATION/ELIMINATION OF β-LACTONES

DOI: 10.1016/S0040-4020(01)82011-1

Source and publish data:

Tetrahedron p. 2307 - 2316 (1990)

Update date:2022-08-05

Topics:

Authors:

Black, T. Howard

Eisenbeis, Shane A.

McDermott, Todd S.

Maluleka, Stephen L.

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Article abstract of DOI:10.1016/S0040-4020(01)82011-1

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 E1-type mechanism is also provided.

Full text of DOI:10.1016/S0040-4020(01)82011-1

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