SYNTHETIS OF CYCLIC AND ACYCLIC β,γ-UNSATURATED CARBOXYLIC ACIDS VIA AN E1-TYPE IONIZATION/ELIMINATION OF β-LACTONES
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.
Black, T. Howard,Eisenbeis, Shane A.,McDermott, Todd S.,Maluleka, Stephen L.
p. 2307 - 2316
(2007/10/02)
AN EFFICIENT, HIGHLY REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED (1-CYCLOHEXENYL) ACETIC ACID DERIVATIVES VIA IONIZATION/ELIMINATION OF β-LACTONES
When treated with magnesium bromide, spiro β-lactones undergo an ionization/elimination reaction to afford cyclohexenyl acetic acid derivatives in high yield and isomeric purity.
Black, T. Howard,Maluleka, Stephen L.
p. 531 - 534
(2007/10/02)
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