13881-40-8Relevant articles and documents
Bromolysis and iodolysis of α,β-epoxycarboxylic acids in water catalyzed by indium halides
Amantini,Fringuelli,Pizzo,Vaccaro
, p. 4463 - 4467 (2007/10/03)
The ring opening of α,β-epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-β-monoalkylated epoxycarboxylic acids at pH 4.0 was completely α-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of α,β-epoxycarboxylic acids at pH 1.5 gave the corresponding anti β-iodohydrins in 88-95% yields. The one-pot synthesis of the α- and β-hydroxyhexanoic acids, starting from the corresponding α,β-epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.
Etude par la Modelisation Moleculaire de la Regioselectivite de l'Ouverture des Acides Glycidiques par les Amines Aliphatiques
Grosjean, F.,Huche, M.,Larcheveque, M.,Legendre, J. J.,Petit, Y.
, p. 9325 - 9334 (2007/10/02)
A model for glycidic acids opening reaction by ammonia and amines has been suggested from semi-empiric orbital calculations.It provides a way for evaluating the different interactions between the incoming nucleophile and the oxirane substituents.Steric and coulombic interactions of the carboxylate in staggered conformation (cis substitution) has a major influence to rationalize experimental regioselectivity.
Reaction of N haloamide. XX. Bromo formyloxylation of α,β unsaturated esters with N,N dibromobenzenesulfonamide and formic acid
Ueno,Yamasaki,Terauchi,Takemura
, p. 1646 - 1651 (2007/10/06)
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