33367-54-3Relevant academic research and scientific papers
Scope and mechanism of the electrochemical Reformatsky reaction of α-haloesters on a graphite powder cathode in aqueous anolyte
De Souza, Carlos A.,Navarro, Marcelo,Bieber, Lothar W.,Areias, Madalena C.C.
, p. 118 - 126 (2014/05/06)
Six α-haloesters and eighteen carbonyl compounds were submitted to electrochemical coupling on a graphite powder cathode using aqueous anolyte free of organic solvents. Preparative yields of coupling products could be obtained with ethyl 2-bromoisobutyrate and aromatic aldehydes. Ethyl 2-bromopropionate was much less efficient. Extensive variation of applied potential, electrolyte composition, stoichiometry, catalyst, leaving halogen and activating substituents on the carbonyl compound led to the conclusion that the reaction mechanism in most cases proceeds via a radical intermediate generated from the halide reduction. Ethyl chloroacetate produced only trace amounts of coupling product, most probably by a carbanionic mechanism.
Behaviour of ot-carbethoxy radical generated from the ester of N-hydroxy-2-thiopyridone
Borah, Ruli,Sarma, Jadab C.
, p. 533 - 535 (2007/10/03)
Studies on the behaviour of α-carbethoxy radical generated from the ester of N-hydroxy-2-thiopyridone is described.
Electrochemical activation of zinc in the coupling reaction of α-bromoesters with carbonyl compounds
Rollin, Y.,Gebehenne, C.,Derien, S.,Dunach, E.,Perichon, J.
, p. 9 - 14 (2007/10/02)
The Reformatsky reaction has been examined using a mild and effective method of electrochemical zinc activation, based on the cathodic reduction of a catalytic amount of zing bromide in acetonitrile.
Pentacarbonylmanganese enolate and dienolate complexes. Preparative and mechanistic considerations
Masters, Andrew P.,Sorensen, Ted S.
, p. 492 - 501 (2007/10/02)
Reactions of pentacarbonyl manganate anion with 4-halocrotonate esters or 2-halocarboxylate esters result in a complex set of inorganic and organic products, usually including the expected dienolate (or enolate) complexes.The reaction variables include the counterion, solvent, and halo group.The mechanism of the reaction has been investigated by conducting a thorough characterization of the reaction products under various conditions and also by carrying out model reactions.One can rationalize most of the non-organometallic products using either a radical or carbanion mechanism, but the latter seems to fit the available data better.Experimental procedures for optimizing the yield of the organometallic dienolate or enolate complexes have been worked out.
Intramolecular hydride shift in some noncyclic isopropyl ketols
Warnhoff, E. W.,Wong, Margaret Y. H.,Raman, P. Sundara
, p. 688 - 696 (2007/10/02)
The acyclic ketols 711 and 812 have been synthesized by a Reformatsky sequence.Each ketol undergoes intramolecular hydride transfer when refluxed in KOH-H2O-t-BuOH solution.When the procedure was applied to the synthesis of 34, hydride transfer ocur
Synthesis of 1,1-Diphenylaminoalcohols
Bertram, Juergen
, p. 44 - 51 (2007/10/02)
The synthesis of 2-amino-2-methyl-1,1-diphenyl-1-propanol (2a) and some of its aryl- and N-substituted derivatives from amino acid esters and Grignard compounds is described.The limits of this synthesis are reported, and so are other methods for the synthesis of amino alcohols.
