2205-24-5Relevant academic research and scientific papers
Thallium trinitrate mediated oxidation of 3-alkenols: Ring contraction vs cyclization
Ferraz, Helena M. C.,Longo Jr., Luiz S.,Zukerman-Schpector, Julio
, p. 3518 - 3521 (2007/10/03)
The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.
SYNTHETIS OF CYCLIC AND ACYCLIC β,γ-UNSATURATED CARBOXYLIC ACIDS VIA AN E1-TYPE IONIZATION/ELIMINATION OF β-LACTONES
Black, T. Howard,Eisenbeis, Shane A.,McDermott, Todd S.,Maluleka, Stephen L.
, p. 2307 - 2316 (2007/10/02)
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.
AN EFFICIENT, HIGHLY REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED (1-CYCLOHEXENYL) ACETIC ACID DERIVATIVES VIA IONIZATION/ELIMINATION OF β-LACTONES
Black, T. Howard,Maluleka, Stephen L.
, p. 531 - 534 (2007/10/02)
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.
Enecarboxylation with Diethyl Oxomalonate as an Enophilic Equivalent of Carbon Dioxide. A Synthesis of Allylcarboxylic Acids
Salomon, Mary F.,Pardo, Simon N.,Salomon, Robert G.
, p. 3797 - 3802 (2007/10/02)
Allylcarboxylic acids are prepared from alkenes by a two-stage process which is synthetically equivalent to an ene reaction of carbon dioxide: (1) ene reaction with diethyl oxomalonate to afford an α-hydroxylmalonic ester and (2) oxidative bisdecarboxylation of the derived α-hydroxymalonic acid.The oxidative bisdecarboxylation of α-hydroxymalonic acids can sometimes be achieved with sodium periodate.However, occasionally decarboxylation is only partial, leading to pyruvic rather than carboxylic acids.While the bisdecarboxylations with periodate have previously been "buffered with a little pyridine", the latter is now shown to inhibit the reaction.In fact the pyruvate:carboxylate ratio can be a sensitive function of the amount of pyridine present in the reaction mixture, and the oxidative decarboxylation can be controlled to yield almost exclusively carboxylic or pyruvic acid.An effective new reagent, ceric ammonium nitrate in aqueous acetonitrile, was discovered for oxidative bisdecarboxylation of α-hydroxymalonic acids.Fortunately this reagent provides good to excellent yields of allylcarboxylic acids in many cases for which sodium periodate proved unsatisfactory.
